Pyridine → HCID 22951550, compound

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (0.046 mL, 0.36 mmol) is added dropwise to DMF (5 mL), and the resulting solution is cooled to 0° C. After the solution is clear, pyridine (0.032 mL, 0.40 mmol) is added, followed by N-[3-methyl-N-(2,2-diphenylacetyl)-L-phenylalanyl]-O-[[5-(methoxycarbonyl)-fur-2-yl]-methyl]-L-serinamide (0.20 g, 0.33 mmol), in one portion. The yellow reaction solution is stirred at 0° C. for 1.5 hours, after which time it is diluted with EtOAc (50 mL), and washed with saturated NaHCO3 (1×50 mL), saturated LiCl (1×50 mL), dried over MgSO4, and evaporated. The residue is chromatographed (silica, 40% EtOAc/hexane) to yield N-[2-[(5-(methoxycarbonyl)-fur-2-yl)-methoxy]-1(S)-cyanoethyl]-3-methyl-Nα-(2,2-diphenylacetyl)-L-phenylalaninamide as a white solid.

Provenance & Evidence