Methods of making (s)-3-(aminomethyl)-5-methylhexanoic acid

Details Methods of making (s)-3-(aminomethyl)-5-methylhexanoic acid Methods of making (s)-3-(aminomethyl)-5-methylhexanoic acid

C - Chemistry, Metallurgy

07

C

C07C 229/08 (2006.01) C07C 211/27 (2006.01) C07C 227/26 (2006.01) C07C 227/32 (2006.01) C07C 233/05 (2006.01) C07C 235/74 (2006.01)

Patent

CA 2219278

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 (t)-3-(carbamoylmethyl)-5-methylhexanoic acid with (R)-(+)-.alpha.-phenylethylamine to obtain the (R)-(+)-.alpha.- 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.

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)-(+)- alpha -phényléthylamine de manière à obtenir le sel (R)-(+)- alpha -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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