Diisopropylethylamine → Methyl 2-[n-methyl-n-((r/s)-alpha-methyl-4-benzyloxyphenylacetyl)amino]-(r)-propionate

Participants

Reaction Steps

To a solution of (R/S)-α-methyl-4-benzyloxyphenylacetic acid 45b (300 mg, 1.17 mmol) and N-methyl-D-alanine methyl ester (200 mg, 1.3 mmol) in DMF (5 mL) cooled in an ice bath was added BOP (531 mg, 1.2 mmol) followed by DIEA (0.7 mL, 4 mmol). The mixture was stirred at room temperature for 5 hours. EtOAc was added and the solution washed with NaHCO3, brine, citric acid and brine, dried (MgSO4), and concentrated. Purification on a silica gel column (40% EtOAc/hexane) gave the amide product (398 mg, 99%) as a solid. MS (CI—NH3): (M+H)+=356.

Provenance & Evidence