Phosgene → 1-({4-(tert-Butyl-dimethyl-silanyloxy)-1-[hept-6-enyl-(4-methoxy-benzyl)-carbamoyl]-pyrrolidine-2-carbonyl}-amino)-2-vinyl-cyclopropanecarboxylic acid ethyl ester

Participants

Reaction Steps

Compound 124 (5.88 g, 15.4 mmol) was dissolved in THF (200 ml), NaHCO3 (s) (appr. 10 ml) was added followed by phosgene-solution (20% in toluene, 15.9 ml, 30.7 mmol). The reaction mixture was stirred vigorously for 1 h and then filtrated, evaporated and redissolved in DCM (200 ml). NaHCO3 (s) (appr. 10 ml) was added followed by hept-6-enyl-(4-methoxy-benzyl)-amine (5.58 g, 23.9 mmol). The reaction mixture was stirred at room temperature overnight, filtrated and evaporated on silica. The crude product was purified by column chromatography on silica (EtOAc/n-Heptane 25/75-50/50) to give the title compound (4.9 g, 50%).

Provenance & Evidence