反应详情

A solution of 53.0 g (333 mmol) of sulfur trioxide pyridine complex in 300 mL of dimethylsulfoxide was added to a solution of 8.64 g (34.4 mmol) of benzyl (5S)-5-{[t-butyloxycarbonyl]amino}-6-hydroxyhexylcarbamate and 14.4 mL (103 mmol) of triethylamine in 130 mL of dichloromethane at 0° C. The cold bath was removed, and the reaction mixture was stirred for 23 h. It was then poured slowly into a mixture of ice and 1 L of saturated aqueous sodium chloride. The resulting mixture was extracted with three 600 mL portions of ether. The ether extracts were then combined, washed with three 150 mL portions of saturated aqueous sodium chloride, and concentrated to 1.2 L. The concentrated ether phase was further washed with three 200 mL aliquots of 5% aqueous citric acid, and a 200 mL portion of saturated aqueous sodium chloride. After drying over magnesium sulfate, volatiles were removed under vacuum to afford 37.58 g (93%) of (2S)-6-{[(benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]hexanal. 1H NMR (300 MHz, DMSO-d6) δ 9.44 (s, 1H), 7.46-7.23 (m, 6H), 5.02 (s, 2H), 3.85-3.75 (m, 1H), 3.07-2.93 (m, 2H), 1.77-1.60 (m, 1H), 1.56-1.23 (m, 5H), 1.41 (s, 9H).

1. customThe cold bath was removed
2. additionIt was then poured slowly into a mixture of ice and 1 L of saturated aqueous sodium chloride
3. extractionThe resulting mixture was extracted with three 600 mL portions of ether
4. washwashed with three 150 mL portions of saturated aqueous sodium chloride
5. concentrationconcentrated to 1.2 L
6. washThe concentrated ether phase was further washed with three 200 mL aliquots of 5% aqueous citric acid
7. dry with materialAfter drying over magnesium sulfate, volatiles
8. customwere removed under vacuum