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1. WO1996038405 - METHODS OF MAKING (S)-3-(AMINOMETHYL)-5-METHYLHEXANOIC ACID

Publication Number WO/1996/038405
Publication Date 05.12.1996
International Application No. PCT/US1996/005831
International Filing Date 26.04.1996
Chapter 2 Demand Filed 09.12.1996
IPC
C07C 211/27 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
211Compounds containing amino groups bound to a carbon skeleton
01having amino groups bound to acyclic carbon atoms
26of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
27having amino groups linked to the six-membered aromatic ring by saturated carbon chains
C07C 227/32 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
227Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
30Preparation of optical isomers
32by stereospecific synthesis
C07C 229/08 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
229Compounds containing amino and carboxyl groups bound to the same carbon skeleton
02having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
04the carbon skeleton being acyclic and saturated
06having only one amino and one carboxyl group bound to the carbon skeleton
08the nitrogen atom of the amino group being further bound to hydrogen atoms
C07C 233/05 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
233Carboxylic acid amides
01having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
02having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
04with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic saturated carbon skeleton
05having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
CPC
C07C 211/27
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
211Compounds containing amino groups bound to a carbon skeleton
01having amino groups bound to acyclic carbon atoms
26of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
27having amino groups linked to the six-membered aromatic ring by saturated carbon chains
C07C 227/32
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
227Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
30Preparation of optical isomers
32by stereospecific synthesis
C07C 229/08
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
229Compounds containing amino and carboxyl groups bound to the same carbon skeleton
02having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
04the carbon skeleton being acyclic and saturated
06having only one amino and one carboxyl group bound to the carbon skeleton
08the nitrogen atom of the amino group being further bound to hydrogen atoms
C07C 233/05
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
233Carboxylic acid amides
01having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
02having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
04with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
05having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
Applicants
  • WARNER-LAMBERT COMPANY [US]/[US]
Inventors
  • HUCKABEE, Brian, Keith
  • SOBIERAY, Denis, Martin
Agents
  • RYAN, M., Andrea
  • MANSMANN, Ivo
Priority Data
08/458,95002.06.1995US
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) METHODS OF MAKING (S)-3-(AMINOMETHYL)-5-METHYLHEXANOIC ACID
(FR) PROCEDES DE PRODUCTION D'ACIDE (S)-3-(AMINOMETHYL)-5-METHYLHEXANOIQUE
Abstract
(EN)
The present invention provides a method of making (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid which comprises condensing isovaleraldehyde with an alkyl cyanoacetate to form a 2-cyano-5-methylhex-2-enoic acid alkyl ester; reacting the 2-cyano-5-methylhex-2-enoic acid alkyl ester with a dialkyl malonate to form 3-isobutylglutaric acid; forming the anhydride of 3-isobutylglutaric acid; reacting the anhydride with ammonia to form (±)-3-(carbamoylmethyl)-5-methylhexanoic acid; reacting (±)-3-(carbamoylmethyl)-5-methylhexanoic acid with (R)-(+)-$g(a)-phenylethylamine to obtain the (R)-(+)-$g(a)-phenylethylamine salt of (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid; combining the salt with an acid to obtain (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid; and reacting the (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid with a Hofmann reagent to obtain (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid.
(FR)
La présente invention concerne un procédé de production d'acide (S)-(+)-3-(aminométhyl)-5-méthylhexanoïque, lequel procédé comprend les étapes suivantes: concentrer de l'isovaléraldéhyde avec un cyanoacétate d'alkyle de manière à former un ester d'alkyle d'acide 2-cyano-5-méthylhex-2-énoïque; faire réagir l'ester d'alkyle d'acide 2-cyano-5-méthylhex-2-énoïque avec un malonate de dialkyle de manière à former de l'acide 3-isobutylglutarique; former l'anhydride de l'acide 3-isobutylglutarique; faire réagir cet anhydride avec de l'ammoniac de manière à former de l'acide (±)-3-(carbamoylméthyl)-5-méthylhexanoïque; faire réagir l'acide (±)-3-(carbamoylméthyl)-5-méthylhexanoïque avec (R)-(+)-$g(a)-phényléthylamine de manière à obtenir le sel (R)-(+)-$g(a)-phényléthylamine de l'acide(R)-(-)-3-(carbamoylméthyl)-5-méthylhexanoïque; combiner ce sel avec un acide de manière à obtenir de l'acide (R)-(-)-3-(carbamoylméthyl)-5-méthylhexanoïque; et, enfin, faire réagir l'acide (R)-(-)-3-(carbamoylméthyl)-5-méthylhexanoïque avec un réactif de Hofmann de manière à obtenir de l'acide (S)-(+)-3-(aminométhyl)-5-méthylhexanoïque.
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