Triphosgene → HCID 71113069, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N1-[4-(1,3-dihydro-2-benzofuran-5-yloxy)phenyl]-D-alaninamide (Intermediate 77, 100 mg, 0.335 mmol) and TEA (0.234 ml, 1.676 mmol) in dichloromethane (10 ml) was stirred under argon at 0° C. Triphosgene (49.7 mg, 0.168 mmol) in dichloromethane (4 ml) was added and the mixture was left stirring at 0° C. for 15 minutes. After 30 min an aqueous saturated solution of NaHCO3 was added. The phases were separated and the aqueous phase was extracted 3 times with dichloromethane. The gathered organic phases were dried over sodium sulphate and concentrated under vacuum. The residue obtained was purified by flash chromatography (Biotage SP1), using as eluents a gradient cyclohexane/ethyl acetate 90:10 to 65:45 to 20:80. This afforded the title compound (20 mg).

Provenance & Evidence