Acetic Acid → HCID 71651084, compound

Participants

Reaction Steps

A mixture of methyl 1-{[2-(3,5-difluorophenyl)-2-oxoethyl]amino}cyclopentanecarboxylate from Step A (10.0 g, 33.6 mmol), glycine ethyl ester hydrochloride (46.9 g, 336 mmol), and AcOH (5.78 mL, 101 mmol) in MeOH (300 mL) was stirred at ambient temperature for 10 min. NaCNBH3 (2.54 g, 40.4 mmol) was added and the pH of the mixture was checked and adjusted to pH˜5 as necessary by addition of AcOH. The reaction mixture was heated to 50° C. for 18 h then allowed to cool. The reaction mixture was carefully quenched with saturated aqueous NaHCO3 (250 mL) and then extracted with CH2Cl2 (3×200 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with hexane:EtOAc-100:0 to 0:100, to give the title compound. MS: m/z=353 (M+1).

Provenance & Evidence