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Optical resolution of 3-carbamoylmethyl-5-methyl hexanoic acid

a technology of hexanoic acid and optical resolution, which is applied in the direction of organic chemistry, drug compositions, organic racemisation, etc., to achieve the effect of improving the optical purity of (r)—cmh

Inactive Publication Date: 2007-12-13
HEDVATI LILACH +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The process achieves (R)-CMH with less than 0.2% impurity by HPLC, overcoming the limitations of previous methods by avoiding carcinogenic solvents and improving the efficiency of enantiomer recycling, resulting in high optical purity and economic viability.

Problems solved by technology

However, the optical resolution is done using a mixture of EtOH and chloroform, and therefore is problematic.

Method used

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  • Optical resolution of 3-carbamoylmethyl-5-methyl hexanoic acid
  • Optical resolution of 3-carbamoylmethyl-5-methyl hexanoic acid
  • Optical resolution of 3-carbamoylmethyl-5-methyl hexanoic acid

Examples

Experimental program
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Effect test

example 1

Optical Resolution of (R)—CMH-Ephedrine Salt

[0082] A 250 ml flask was charged with 100 ml of acetone, 10 ml of methanol, 10 g of CMH-racemate, and 4.4 g of 1R,2S-(−)-ephedrine. The resulting clear solution was evaporated to dryness, and 100 ml of acetone was added to the residue. After stirring for 1 hour at room temperature, the precipitate was filtered, washed with 40 ml of acetone, and dried at 45° C. at a pressure of 10 mm Hg. The (R)—CMH-ephedrine salt was found to have an optical purity of 99.3% area by HPLC.

example 2

Optical Resolution of (R)—CMH-Ephedrine Salt

[0083] A 100 ml flask was charged with 40 ml of acetone, 5 g of CMH-racemate, and 4.4 g of 1R,2S-(−)-ephedrine. The mixture was heated to dissolution, and then cooled to 10° C. After stirring for 1 hour at 10° C., the resulting precipitate was filtered, washed with 10 ml of acetone, and dried at 45° C. at a pressure of 10 mm Hg. The (R)—CMH-ephedrine salt was found to have an optical purity of 97% area by HPLC.

example 3

Optical Resolution of (R)—CMH-Ephedrine Salt

[0084] A 100 ml flask was charged with acetone (80 ml), CMH-racemate (10 gr), Triethylamine (5.4 gr) and 1R,2S-(−)-Ephedrine hydrochloride (10.79 gr). The mixture was heated to reflux and stirred at reflux for 2 h. The mixture was cooled to 10° C., and after stirring for 1 h at 10° C. the precipitate was filtered, washed with acetone (10 ml) and dried at 45° C. under 10 mm Hg. (R)—CMH-ephedrine salt was obtained (9.95 gr), 90.2% optical pure.

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Abstract

The invention relates to pure (R)—CMH and to the optical resolution of CMH-racemate, a key intermediate in the synthesis of (S)-Pregabalin. The invention also relates to the process for optically purifying (R)—CMH and to the process for isolating (S)—CMH from the mother liquor.

Description

RELATED APPLICATIONS [0001] This application is a divisional of U.S. patent application Ser. No. 11 / 432,010, filed May 10, 2006, which claims the benefit of priority to U.S. provisional application Nos. 60 / 679,784, filed May 10, 2005, 60 / 689,699, filed Jun. 9, 2005, 60 / 733,009, filed Nov. 2, 2005, 60 / 735,634, filed Nov. 9, 2005, and 60 / 740,950, filed Nov. 29, 2005, the contents of which are incorporated herein by reference in their entirety.FIELD OF THE INVENTION [0002] The present invention is directed to pure (R)—CMH, the optical resolution of 3-carbamoylmethyl-5-methyl hexanoic acid-racemate (CMH-racemate), the process for optically purifying (R)—CMH and the process for isolating (S)—CMH from the mother liquor. BACKGROUND OF THE INVENTION [0003] (S)-Pregabalin, (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid, a compound having the chemical structure, is also known as γ-amino butyric acid or (S)-3-isobutyl GABA. (S)-Pregabalin has been found to activate GAD (L-glutamic acid decarb...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07B57/00
CPCC07C215/30C07C227/16C07C229/08C07C231/20C07C233/05A61P25/08C07C233/18
Inventor HEDVATI, LILACHDEE-NOOR, ZIVSINGER, CLAUDEPILARSKI, GIDEON
Owner HEDVATI LILACH
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