Nitrogen → HCID 86589057, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-(5-(3-methoxycarbonylphenyl)-1(S)-cyanopentyl]-3-methyl-Nα-(3-oxo-1,3-dihydro-isobenzofuran-5-yl)-L-phenylalaninamide (0.354 g, 0.67 mmol) in pinacolone (15 mL) is deoxygenated with bubbling N2 for 5 min., after which time Lil (0.90 g, 6.74 mmol) is added in one portion. The solution is then heated to 100° C. for 28 h. After cooling, it is diluted with EtOAc (100 mL), and washed with 1 N HCl (100 mL), and brine (50 mL), then dried (MgSO4), evaporated and chromatographed (2% MeOH/CH2Cl2, 0% to 0.05% acetic acid) to yield N-(5-(3-carboxyphenyl)-1(S)-cyanopentyl]-3-methyl-Nα-(3-oxo-1,3-dihydro-isobenzofuran-5-yl)-L-phenylalaninamide, as a light yellow solid; m.p. 91-94° C.

Provenance & Evidence