Hydrochloric Acid → HCID 10771214, compound

Participants

Reaction Steps

To a solution of the objective compound of step (14) (69 g, 95 mmol) and WSCIHCl (99.87 g, 0.5209 mol) in DMSO (590 mL)-toluene (590 mL) was added dichloroacetic acid (15.6 mL) with drop wise over 20 minutes under ice-cooling. The resulting mixture was stirred under ice-cooling for 2.5 hours, then added to 0.5 M hydrochloric acid (1800 mL) and extracted with ethyl acetate (1800 mL, 2×800 mL). The extract was washed with saturated sodium hydrogencarbonate aqueous solution (800 mL) and saturated brine (800 mL), dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (99:1 chloroform-methanol) to give 52.95 g (77%) of 2-[5-benzyloxycarbonylamino-2-(3-chlorophenyl)-1,6-dihydro-6-oxo-1-pyrimidinyl]-N-[1-benzyl-3-[N-(benzyl)carbamoyl]-3,3-difluoro-2-oxopropyl]acetamide as a white solid.

Provenance & Evidence