Method of making (S)-3-(aminomethyl)-5-methylhexanoic acid

Details Method of making (S)-3-(aminomethyl)-5-methylhexanoic acid Method of making (S)-3-(aminomethyl)-5-methylhexanoic acid

1995-06-07

1997-06-10

Shippen, Michael L.

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

Organic compounds

Carboxylic acids and salts thereof

562401, C07L20500

Patent

active

056377673

ABSTRACT:
A method of making (.+-.)-3-(aminomethyl)-5-methylhexanoic acid that comprises condensing isovaleraldehyde with ##STR1## to form primarily ##STR2## reacting the ##STR3## with a cyanide source to form ##STR4## decarboxylating the ##STR5## to form ##STR6## hydrolyzing the ##STR7## with an alkali or alkaline earth metal hydroxide to form an alkali or alkaline earth metal carboxylate salt; and hydrogenating the alkali or alkaline earth metal carboxylate salt to form (.+-.)-3-(aminomethyl)-5-methylhexanoic acid, wherein R.sub.1 and R.sub.2 are the same or different and are hydrogen, C.sub.1 -C.sub.6 alkyl, aryl, benzyl, or C.sub.3 -C.sub.6 cycloalkyl. The present invention also provides a method of making (.+-.)-3-(aminomethyl)-5-methylhexanoic acid that comprises condensing isovaleraldehyde with ##STR8## to form primarily ##STR9## reacting the ##STR10## with a cyanide source to form ##STR11## decarboxylating the ##STR12## to form an alkali or alkaline earth metal carboxylate salt; and hydrogenating the alkali or alkaline earth metal carboxylate salt to form (.+-.)-3-(aminomethyl)-5-methylhexanoic acid.

REFERENCES:
patent: 5132451 (1992-07-01), Jennings et al.
Carruthers, et al., Bioorganic & Medicinal Chemistry Letters, vol. 5, No. 3, pp. 237-240 (1995) Andruszkiewicz, et al., Synthesis, pp. 953-955 (1989).
Jung, et al., Biochemistry, vol. 17, No. 13, pp. 2628-2632 (1978).

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