Water → HCID 67490915, compound

Participants

Reaction Steps

N-(Benzyloxycarbonyloxy)succinimide (1.49 g, 5.98 mmol) was added to a solution of (2R*,3R*)-3-amino-2-(tert-butoxycarbonylamino)methyl-3,4,5,6-tetrahydro-2H-pyrane-3-carboxylic acid (1.09 g, 3.99 mmol) and triethylamine (1.11 mL, 7.96 mmol) in tetrahydrofuran (10 mL)/water (10 mL) under ice-cooling, and the mixture was stirred at room temperature for 15 hours. The reaction solution was diluted with ethyl acetate (150 mL) and washed with 1N hydrochloric acid (50 mL). The resulting organic layer was dried over anhydrous sodium sulfate and filtered. Then, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol:chloroform=2:98→5:95) and then dissolved in a 1N sodium hydroxide solution (50 mL) and washed with diethyl ether (2×20 mL) to remove the remaining benzyl alcohol. The resulting aqueous layer was adjusted to pH 1 to 2 with concentrated hydrochloric acid, followed by extraction with dichloromethane (2×80 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and filtered. Then, the solvent was evaporated under reduced pressure to obtain 1.08 g (66%) of the title compound as a white solid.

Provenance & Evidence