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

1995-06-02

1997-04-01

Shippen, Michael L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acids and salts thereof

C07C20500

Patent

active

056167938

ABSTRACT:
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)-(+)-.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.

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