A practical 4-step synthesis of fibrinogen receptor antagonist MK-383, N-(n-butanesulfonyl)- O-(4-(4-piperidinyl)-butyl)-(S)-tyrosine, is accomplished in 48% overall yield from (S)- tyrosine. Highlights include:(1) the dual use of 4-picoline as a masked form of piperidine, and as a nucleophile precursor for a 3-carbon homologation with 3-bromo-1- chloropropane;(2) the use of trimethylsilyl groups for temporary protection of phenolic and ...
