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Refining method of high-purity R-(-)-3-carbamylmethyl-5-methylhexanoic acid

The technology of carbamoylmethyl and methylhexanoic acid is applied in the field of organic synthesis and refining, and can solve the problem of low purity of chiral monomer, R-(-)-3-carbamoylmethyl-5-methyl Insufficient purity of hexanoic acid, etc., to achieve the effect of high purity and good process stability

Pending Publication Date: 2021-12-03
江西金丰药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Aiming at the problems of insufficient purity of R-(-)-3-carbamoylmethyl-5-methylhexanoic acid prepared in the prior art and low purity of chiral monomers, the present invention provides a high-purity R-(- The refining method of )-3-carbamoylmethyl-5-methylhexanoic acid

Method used

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  • Refining method of high-purity R-(-)-3-carbamylmethyl-5-methylhexanoic acid
  • Refining method of high-purity R-(-)-3-carbamylmethyl-5-methylhexanoic acid

Examples

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Embodiment 1

[0030] 1. Put in 100g (±)-3-carbamoylmethyl-5-methylhexanoic acid, 2235g chloroform, 67g absolute ethanol, heat up to 55°C to dissolve, add 65g R-phenylethylamine, cool to 32± Filter at 1°C to obtain the wet product of R-(-)-3-carbamoylmethyl-5-methylhexanoic acid phenethylamine salt. Add the wet product of R-(-)-3-carbamoylmethyl-5-methylhexanoic acid phenethylamine salt and 187g of water into the reaction flask, heat up to 65°C to dissolve, let stand to separate layers, and the water layer is usually Pressure distillation to 72°C, then lower the temperature to below 40°C, add 47g of hydrochloric acid dropwise until the pH is 1-2, then cool to 25°C, heat and crystallize for more than 1 hour, filter with suction, rinse with water, and get R-(-)- 43 g of crude wet product of 3-carbamoylmethyl-5-methylhexanoic acid (38.2 g on dry basis, purity 94%, e.e. value 97.2%).

[0031] 2. Add 43g of the obtained R-(-)-3-carbamoylmethyl-5-methylhexanoic acid crude wet product, 90g of ethy...

Embodiment 2

[0033] 1. Put in 100g (±)-3-carbamoylmethyl-5-methylhexanoic acid, 2235g chloroform, 67g absolute ethanol, heat up to 55°C to dissolve, add 65g R-phenylethylamine, cool to 32± Filter at 1°C to obtain the wet product of R-(-)-3-carbamoylmethyl-5-methylhexanoic acid phenethylamine salt. Add the wet product of R-(-)-3-carbamoylmethyl-5-methylhexanoic acid phenethylamine salt and 187g of water into the reaction flask, heat up to 65°C to dissolve, let stand to separate layers, and the water layer is usually Pressure distillation to 72°C, then lower the temperature to below 40°C, add 47g of hydrochloric acid dropwise until the pH is 1-2, then cool to 25°C, heat and crystallize for more than 1 hour, filter with suction, rinse with water, and get R-(-)- 41 g of crude wet product of 3-carbamoylmethyl-5-methylhexanoic acid (37.4 g on dry basis, purity 95.2%, e.e. value 97.6%).

[0034] 2. Add 41g of the obtained R-(-)-3-carbamoylmethyl-5-methylhexanoic acid crude wet product, 90g of et...

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Abstract

The invention discloses a refining method of high-purity R-(-)-3-carbamylmethyl-5-methylhexanoic acid, and belongs to the technical field of organic synthesis and refining. The method comprises the following steps of: salifying (+ / -)-3-carbamylmethyl-5-methylhexanoic acid serving as a raw material and R-phenylethylamine in a mixed solvent of alcohol and halogenated hydrocarbon to prepare R-(-)-3-carbamylmethyl-5-methylhexanoic acid phenylethylamine salt; dissolving in water, and acidifying to obtain an R-(-)-3-carbamylmethyl-5-methylhexanoic acid crude product; and finally, mixing ethyl acetate and water, and refining to obtain a high-purity R-(-)-3-carbamylmethyl-5-methylhexanoic acid product, wherein the e.e. Value of the high-purity R-(-)-3-carbamylmethyl-5-methylhexanoic acid product is not less than 99.5%. Compared with other refining methods, the R-(-)-3-carbamylmethyl-5-methylhexanoic acid refining method disclosed by the invention has the advantages that the product purity is higher, and the process stability is good.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and refining, in particular to a method for refining high-purity R-(-)-3-carbamoylmethyl-5-methylhexanoic acid. Background technique [0002] R-(-)-3-carbamoylmethyl-5-methylhexanoic acid is a key intermediate of pregabalin, an r-aminobutyric acid (GABA) receptor antagonist developed by Pfizer. Pregabalin was approved by the European Union in July 2004 and was first launched in the UK as an adjuvant epilepsy drug for some patients with epileptic seizures. Compared with the clinically used gabapentin, pregabalin has stronger anticonvulsant effect, less adverse reaction history, low dose, less frequent administration, and anti-anxiety effect. It is a replacement product of gabapentin and has a broad market prospect. [0003] In existing literature, R-(-)-3-carbamoylmethyl-5-methylhexanoic acid is synthesized by (±)-3-carbamoylmethyl-5-methylhexanoic acid through a series of reactions get...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/05C07C231/12
CPCC07C231/12C07C233/05
Inventor 聂丰彬占付灵柯维贤
Owner 江西金丰药业有限公司
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