4-Methylmorpholine → 2-(2-Tert-butoxycarbonylamino-4-phenyl-butyrylamino)-3-methylbutyric acid methyl ester

Participants

Reaction Steps

To an ice-cooled solution of D-valine methyl ester hydrochloride (1000 mg, 3.58 mmol) and HOBt (in DMF (14 mL) was added EDCI (755 mg, 3.94 mmol). After the mixture was stirred for 30 min, N-boc-L-homophenylalanine (600 mg, 3.58 mmol) and N-methylmorpholine (1 mL, 8.95 mmol) were added. The mixture was warmed to room temperature and stirred overnight. The solvent was removed and the residue was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic phases were dried over anhydrous Na2SO4. After concentration under reduced pressure, the crude title compound (2000 mg) was obtained and used in the next step without further purification.

Provenance & Evidence