Sodium hydride → 4-Benzyl 1,4-di-tert-butyl (1S)-6-[4-(benzyloxy)phenyl]-1-[(tert-butoxycarbonyl)amino]hexane-1,4,4-tricarboxylate

Participants

Reaction Steps

To a solution of 1.11 g di-tert-butyl (5S)-2-(benzyloxycarbonyl)-5-[(tert-butoxycarbonyl)-amino]hexanedioate (2.19 mmol; see example 12f) in N,N-dimethyl formamide (30 mL) was added under argon atmosphere 96 mg of sodium hydride (60% in oil, 2.40 mmol), and the mixture was stirred for 30 min at room temperature. Subsequently, a solution of 700 mg of 1-(benzyloxy)-4-(2-bromoethyl)benzene (2.40 mmol) in N,N-dimethyl formamide (15 mL) was added, an the mixture was stirred at 60° C. for 3 hours. The mixture was concentrated in vacuo, partitioned between water and ethyl acetate, and the organic layer was washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by preparative HPLC (Method A) to give 413 mg of the target compound in approx. 90% purity (26% purity adjusted yield).

Provenance & Evidence