N-Cbz-d-alanine → HCID 60078292, compound

Participants

Reaction Steps

To a solution of N-[(benzyloxy)carbonyl]-D-alanine (4.46 g), 11% dimethylamine methanol solution (11.0 mL) and N-ethyl-N-(1-methylethyl)propan-2-amine (5.17 g) in DMF (30 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (8.37 g) under ice-cooling. The reaction mixture was stirred at room temperature overnight, the reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (3.73 g).

Provenance & Evidence