Portal de Periódicos da CAPES

Amino acids and peptides. XVI. A new synthesis of .ALPHA.-phenylglycine and its derivatives.

1975; Pharmaceutical Society of Japan; Volume: 23; Issue: 1 Linguagem: Inglês

10.1248/cpb.23.173

1347-5223

T. OGURI, Takayuki Shioiri, Shun‐ichi Yamada,

Carbohydrate Chemistry and Synthesis

N, N-Diethyl phenylacetamide and N-n-butyl phenylacetamide were respectively α-lithiated, followed by amination with methoxyamine to give α-phenylglycine N, N-diethylamide (IVa) and α-phenylglycine N-n-butylamide (IVc). However, phenylacetamide gave phenylglyoxylamide only and tert-butyl phenylacetate did not undergo the above amination reaction. Benzylisocyanide and N-(diphenylmethylene) benzylamine (VII) were respectively α-lithiated, subjected to carboxylation, followed by acid hydrolysis to give α-phenylglycine (I) in good yields.