Process for preparation of .alpha.-alkyl amino acids

Details Process for preparation of .alpha.-alkyl amino acids Process for preparation of .alpha.-alkyl amino acids

C - Chemistry, Metallurgy

07

D

260/516, 260/525

C07D 209/20 (2006.01) C07C 227/32 (2006.01) C07D 263/20 (2006.01)

Patent

CA 1240700

ABSTRACT OF THE DISCLOSURE A process for preparing .alpha.-alkyl amino acids by enantioretentive .alpha.-alkylation of .alpha.-amino acids is described. The process comprises the steps of con- verting an optically active acyclic .alpha.-amino acid to a 2-aryloxazolidinone compound in which the non-hydrogen substituent at the 4-position and the aryl group are in a cis relationship, stereospecifically alkylating the 2-aryloxazolidinone by first forming an alkali metal enolate by reacting the oxazolidinone compound with a strong base at greatly reduced temperatures followed by reacting the enolate with an alkylating agent, and generating the .alpha.-alkyl-.alpha.-amino acid from the alkylated 2-aryloxazolidinone by alkaline hydrolysis to open the ring followed by hydrolytic or reductive removal of the protecting group. The products are bioactive compounds including some useful as therapeutic agents.

476448

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