Lithium Hydroxide → HCID 22507515, compound

Participants

Reaction Steps

To a mixture of 1-{[1-(2-tert-butoxycarbonylamino-3,3-dimethyl-butyryl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-spiro[2.3]-hexane-1-carboxylic acid methyl ester (60 mg, 0.084 mmol) in 3 mL of THF, 1.5 mL of MeOH and 0.4 mL of H2O was added LiOH (30 mg, 1.5 mmol). The mixture was stirred at rt for 3 days. It was then concentrated and partitioned between sat. aq. NaHCO3 and ether. The aqueous layer was acidified to pH=4 with dilute HCl, and extracted three times with EtOAc. The combined EtOAc extracts were dried over magnesium sulfate, filtered and concentrated to provide 55 mg of 1-{[1-(2-tert-butoxycarbonylamino-3,3-dimethyl-butyryl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-spiro[2.3]hexane-1-carboxylic acid as a white solid (93%). LC-MS: (retention time 1.71 min), MS m/z 701 (M++1) (Method D).

Provenance & Evidence