4-Methylmorpholine → N-[(benzyloxy)carbonyl]-3-[(1-propylbutyl)sulfonyl)alanine

Participants

Reaction Steps

3-[(1-Propylbutyl)sulfonyl]alanine (LXXXIII, 7.8 g, 27 mmole) and N-CBZ succinamide (7.4 g, 30 mmole) are mixed in methylene chloride (100 ml). The reaction is cooled to 0°, and NMM (6.9 g) is added dropwise. The reaction is allowed to warm to 20–25° and stirred for 4 hours at which point HPLC analysis indicated complete reaction. The reaction mixtue is concentrated under reduced pressure and partitioned between ethyl acetate and hydrochloric acid (1 N). The organic phase is washed with water, saline, dried over sodium sulfate, and concentrated under reduced pressure to give N-[(benzyloxy)carbonyl]-3-[(1-propylbutyl)sulfonyl]alanine (LXXXIV) that is used without further purification, M+H=386.

Provenance & Evidence