CN115896188A - Preparation method of high-purity (S) -5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone - Google Patents
Preparation method of high-purity (S) -5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone Download PDFInfo
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- CN115896188A CN115896188A CN202211669614.XA CN202211669614A CN115896188A CN 115896188 A CN115896188 A CN 115896188A CN 202211669614 A CN202211669614 A CN 202211669614A CN 115896188 A CN115896188 A CN 115896188A
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- methoxycarbonyl
- chloro
- hydroxy
- indanone
- racemate
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- NCNGKAPNQHDQBA-NSHDSACASA-N methyl (2s)-6-chloro-2-hydroxy-3-oxo-1h-indene-2-carboxylate Chemical compound ClC1=CC=C2C(=O)[C@@](C(=O)OC)(O)CC2=C1 NCNGKAPNQHDQBA-NSHDSACASA-N 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title abstract description 6
- NCNGKAPNQHDQBA-UHFFFAOYSA-N methyl 6-chloro-2-hydroxy-3-oxo-1h-indene-2-carboxylate Chemical class ClC1=CC=C2C(=O)C(C(=O)OC)(O)CC2=C1 NCNGKAPNQHDQBA-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 17
- 108010084311 Novozyme 435 Proteins 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 239000012452 mother liquor Substances 0.000 claims abstract description 7
- 230000010933 acylation Effects 0.000 claims abstract description 4
- 238000005917 acylation reaction Methods 0.000 claims abstract description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 108090001060 Lipase Proteins 0.000 claims description 2
- 102000004882 Lipase Human genes 0.000 claims description 2
- 239000004367 Lipase Substances 0.000 claims description 2
- 238000006640 acetylation reaction Methods 0.000 claims description 2
- 235000019421 lipase Nutrition 0.000 claims description 2
- BYUCBODSULLYIS-UHFFFAOYSA-N methyl 6-chloro-3-oxo-1,2-dihydroindene-2-carboxylate Chemical compound ClC1=CC=C2C(=O)C(C(=O)OC)CC2=C1 BYUCBODSULLYIS-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 4
- 239000012043 crude product Substances 0.000 abstract description 3
- 125000004122 cyclic group Chemical group 0.000 abstract description 3
- 230000002779 inactivation Effects 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 238000004064 recycling Methods 0.000 abstract description 3
- 238000003889 chemical engineering Methods 0.000 abstract description 2
- 239000012847 fine chemical Substances 0.000 abstract description 2
- 239000005907 Indoxacarb Substances 0.000 description 10
- VBCVPMMZEGZULK-NRFANRHFSA-N indoxacarb Chemical compound C([C@@]1(OC2)C(=O)OC)C3=CC(Cl)=CC=C3C1=NN2C(=O)N(C(=O)OC)C1=CC=C(OC(F)(F)F)C=C1 VBCVPMMZEGZULK-NRFANRHFSA-N 0.000 description 9
- 230000006978 adaptation Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000003285 pharmacodynamic effect Effects 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- QQWRPXADMUGYKQ-UHFFFAOYSA-N O1NN=CC=C1.O1NN=CC=C1 Chemical compound O1NN=CC=C1.O1NN=CC=C1 QQWRPXADMUGYKQ-UHFFFAOYSA-N 0.000 description 1
- -1 Salen organometallic compound Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 1
- KMPWYEUPVWOPIM-LSOMNZGLSA-N cinchonine Chemical compound C1=CC=C2C([C@@H]([C@H]3N4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-LSOMNZGLSA-N 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- VBCVPMMZEGZULK-OAQYLSRUSA-N methyl (4ar)-7-chloro-2-[methoxycarbonyl-[4-(trifluoromethoxy)phenyl]carbamoyl]-3,5-dihydroindeno[1,2-e][1,3,4]oxadiazine-4a-carboxylate Chemical compound C([C@]1(OC2)C(=O)OC)C3=CC(Cl)=CC=C3C1=NN2C(=O)N(C(=O)OC)C1=CC=C(OC(F)(F)F)C=C1 VBCVPMMZEGZULK-OAQYLSRUSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The invention provides a method for synthesizing (S) -5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone, belonging to the technical field of fine chemical engineering. And (2) separating S and R configurations in the 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone racemate obtained from the reaction mother liquor by using lipase Novozyme435 as a catalyst and vinyl acetate as an acylation reagent to obtain the high-content (S) -5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone. The method overcomes the problems that the prior art can not solve the purification and recycling of the crude product of low-content (S) -5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone, has the advantages of easily obtained raw materials, simpler and more convenient operation, higher product purity, no obvious inactivation of the catalyst during cyclic application and the like, and provides a feasible scheme for the resource utilization of the mother liquor extract and the preparation of high-content (S) -5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone in the production process.
Description
Technical Field
The invention belongs to the technical field of fine chemical engineering, and particularly relates to a method for synthesizing a high-purity indoxacarb intermediate (S) -5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone.
Background
Indoxacarb (indoxacarb) is a novel oxadiazine (oxadiazine) insecticide developed by the U.S. Dupont company, is registered as a reduced-risk product in the United states, australia, china and other countries, and is one of ten insecticides in the world at present.
The main synthetic route of indoxacarb is reported in the literature at present, and the reaction equation is as follows:
the indoxacarb has a carbon atom chiral center in a molecular structure, wherein S-indoxacarb has pharmacodynamic activity, and R-indoxacarb has almost no pharmacodynamic activity. Currently, the commercial indoxacarb is mainly concentrated on S: R =9:1. The 5-chlorine-2-methoxycarbonyl-2-hydroxy-1-indanone is an extremely important intermediate in the synthetic process of the indoxacarb, and the drug effect of the indoxacarb is directly determined by the content of the (S) -5-chlorine-2-methoxycarbonyl-2-hydroxy-1-indanone. The technology reported in the literature at present, 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone (S: R = 9:1) is mainly prepared by carrying out asymmetric oxidation by taking a Salen organometallic compound as a catalyst; or the cinchonine is firstly used as a catalyst to prepare S by asymmetric oxidation, R =3:1, and then the S is purified by a solvent to S, R =9:1; however, both methods cannot separate the S type from the R type, so that a large amount of (S) -5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone in mother liquor cannot be recycled, and resource waste is caused.
Disclosure of Invention
The invention aims to provide a method for synthesizing an indoxacarb intermediate (S) -5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone. And (2) separating S and R configurations in the 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone racemate obtained from the reaction mother liquor by using lipase Novozyme435 as a catalyst and vinyl acetate as an acylation reagent to obtain the high-content (S) -5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone. The method overcomes the problems that the prior art can not solve the purification and recycling of the crude product of low-content (S) -5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone, has the advantages of easily obtained raw materials, simpler and more convenient operation, higher product purity, no obvious inactivation of the catalyst during cyclic application and the like, and provides a feasible scheme for the resource utilization of the mother liquor extract and the preparation of high-content (S) -5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone in the production process.
Specifically, the preparation method of (S) -5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone comprises the following steps:
in an organic solvent, taking lipase Novozyme435 as a catalyst and vinyl acetate as an acylation reagent, carrying out acetylation reaction on an R configuration in a 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone racemate, and then separating out in toluene to obtain (S) -5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone.
Further, in the above technical scheme, the organic solvent is one or more of methyl tert-butyl ether, tetrahydrofuran and dioxane.
Further, in the technical scheme, the 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone racemate is extracted from a mother solution, and the racemate refers to that the ratio of the R configuration to the S configuration is approximately 1/1, and is usually 55/45-45/55.
Further, in the above technical solution, the lipase is a commercial immobilized lipase Novozyme 435.
Further, in the technical scheme, the mass ratio of the lipase Novozyme435 to the racemate 5-chloro-2-methoxycarbonyl-1-indanone is 0.5-20% to 1, preferably 1-10% to 1.
Furthermore, in the technical scheme, the molar ratio of the racemate 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone to the vinyl acetate is 1:1-10, preferably 1:1-5.
Further, in the technical scheme, the mass ratio of the racemate 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone to the organic solvent is 1:8-50, preferably 1-35.
Further, in the above technical scheme, the reaction temperature is 5 to 110 ℃, preferably 15 to 40 ℃.
Further, in the above technical scheme, the reaction time is 12 to 50 hours, preferably 15 to 35 hours.
Further, in the above technical scheme, typical reaction operations are as follows:
1) Methyl tert-butyl ether, racemate 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone, lipase Novozyme435 and vinyl acetate are sequentially added into a four-mouth reaction bottle with a stirring thermometer sleeve, and the mixture is stirred for 24 hours under the condition of heat preservation after the addition.
2) Carrying out heat preservation and reduced pressure filtration on the solid-liquid mixed solution obtained in the step 1), leaching a filter cake with a solvent for reuse, combining filtrates, and carrying out reduced pressure desolventizing;
3) Adding toluene into the desolventized material obtained in the step 2), heating to 50-55 ℃, keeping the temperature and stirring for 1h, slowly cooling to 0-5 ℃, keeping the temperature and reducing the pressure for filtering, and drying a filter cake to obtain (S) -5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone.
Advantageous effects of the invention
1. The invention overcomes the problem that the prior art can not solve the problems of purification, recycling and the like of low-content (S) -5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone crude products.
2. The method provided by the invention has the advantages of easily available raw materials, simple and convenient operation, high product purity, no obvious inactivation caused by cyclic application of the catalyst, safety, less harm to human bodies and light environmental pollution, and provides a feasible method for resource utilization of the mother liquor extract and preparation of high-content (S) -5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone in the production process.
Detailed Description
The following examples are presented to enable one of ordinary skill in the art to more fully understand the present invention and are not intended to limit the invention in any way.
Comparative example
In a 250mL four-mouth bottle, adding 151.22g of dichloroethane and 24.06g of 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone (0.10 mol, S.
Example 1
250g of methyl tert-butyl ether, 24.06g of 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone (0.10mol, S, R = 1.08).
Example 2
250g of methyl tert-butyl ether and 24.06g of 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone (0.10mol, S.
Example 3
250g of methyl tert-butyl ether, 24.06g of 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone (0.10mol, S.
The above is only a preferred embodiment of the present invention, and it should be noted that the above preferred embodiment should not be considered as limiting the present invention, and the protection scope of the present invention should be subject to the scope defined by the claims. It will be apparent to those skilled in the art that various modifications and adaptations can be made without departing from the spirit and scope of the invention, and these modifications and adaptations should be considered within the scope of the invention.
Claims (9)
1. A method for synthesizing (S) -5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone is characterized by comprising the following steps:
in an organic solvent, taking lipase Novozyme435 as a catalyst and vinyl acetate as an acylation reagent, carrying out acetylation reaction on an R configuration in a 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone racemate, and then separating out in toluene to obtain (S) -5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone.
2. The method for preparing 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone according to claim 1, which comprises the following steps: the organic solvent is one or more of methyl tert-butyl ether, tetrahydrofuran and dioxane.
3. The method for preparing 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone according to claim 1, which comprises the following steps: the 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone racemate is extracted from mother liquor, and the racemate refers to that the R configuration and the S configuration are 55/45-45/55.
4. The process for producing 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone according to claim 1, which comprises: the lipase is commercial immobilized lipase Novozyme 435.
5. The process for producing 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone according to claim 1, which comprises: the mass ratio of the lipase Novozyme435 to the racemate 5-chloro-2-methoxycarbonyl-1-indanone is 0.005-0.20.
6. The process for producing 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone according to claim 1, which comprises: the molar ratio of the racemate 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone to the vinyl acetate is 1:1-10.
7. The process for producing 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone according to claim 1, which comprises: the mass ratio of the racemate 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone to the organic solvent is 1:8-50.
8. The process for producing 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone according to claim 1, which comprises: the reaction temperature is 5-110 ℃.
9. The process for preparing 5-chloro-2-methoxycarbonyl-2-hydroxy-1-indanone according to any one of claims 1 to 8, which comprises: the reaction time is 12-50h.
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| CN202211669614.XA CN115896188B (en) | 2022-12-25 | 2022-12-25 | Preparation method of high-purity (S) -5-chloro-2-methoxycarbonyl-2-hydroxy-1-indenone |
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Cited By (1)
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| CN118222643A (en) * | 2023-12-20 | 2024-06-21 | 南京科力硕生物科技有限公司 | Method for producing indoxacarb intermediate by utilizing nano ferrous carbonate immobilized hydroxylase |
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| CN118222643A (en) * | 2023-12-20 | 2024-06-21 | 南京科力硕生物科技有限公司 | Method for producing indoxacarb intermediate by utilizing nano ferrous carbonate immobilized hydroxylase |
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