t-butyl alpha-[6(R)-amino-5-oxo-3(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl]acetate → t-Butyl alpha-[6(R)-(1-butoxycarbonyl-3-phenylpropylamino)-5-oxo-3(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl]acetate

Participants

Reaction Steps

345 mg of t-butyl α-[6(R)-amino-5-oxo-3(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl]acetate [prepared as described in Example 16(g)] were N-alkylated with 450 mg of butyl 2-bromo-4-phenylbutyrate in the same manner as in Example 1(h). The reaction product was then subjected to silica gel column chromatography using a 1:40 by volume mixture of ethyl acetate and methylene chloride as eluent, to separate it into two isomers, A and B (ascribed to the asymmetric carbon atom to which the phenethyl group is attached).

Provenance & Evidence