Synthesis of alpha-methyl, alpha-substituted amino acids

Details Synthesis of alpha-methyl, alpha-substituted amino acids Synthesis of alpha-methyl, alpha-substituted amino acids

1999-06-29

2000-03-28

Geist, Gary

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D36308

Patent

active

060433760

ABSTRACT:
An improved process for making chiral, .alpha.-methylated, .alpha.-substituted amino acids of the formula I ##STR1## wherein Y is a hydrogen atom and R.sub.2 is the residue of a natural or unnatural amino acid, in which process an oxazolidinone of the formula II ##STR2## is formed by reacting a protected amino acid of the formula IA ##STR3## wherein Y is a protecting group, with an aldehyde of the formula RCHO, or an equivalent thereof, in the presence of a chlorinating agent and a Lewis acid.
The group R.sub.2 is introduced into the oxazolidinone intermediate of formula II in a conventional manner, and subsequent hydrolysis and deprotection, both carried out in a conventional manner, yield the chiral, .alpha.-methylated, .alpha.-substituted amino acid.

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