Lithium hydroxide, monohydrate → HCID 68705918, compound

Participants

Reaction Steps

A solution of ethyl 3-(5-((R)-2-tert-butoxycarbonylamino-1-phenylpropan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(1-cyanocyclopentyl)benzoate (0.17 g, 0.31 mmol) and LiOH.H2O (65 mg, 1.55 mmol) in 8.1 mL THF and 3.1 mL H2O was stirred at rt overnight. The reaction was concentrated, diluted with H2O, made acidic with 10% citric acid solution and extracted with EtOAc. The combined organic layers were washed with brine. Drying and solvent evaporation gave 3-(5-((R)-2-tert-butoxycarbonylamino-1-phenylpropan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(1-cyanocyclopentyl)benzoic acid. 1H NMR (400 MHz, CDCl3) δ 8.62 (bs, 1H), 8.36 (d, J=1.4 Hz, 2H), 7.28 (m, 3H), 7.09 (d, J=5.7 Hz, 2H), 5.22 (bs, 1H), 3.61 (d, J=13.4 Hz, 1H), 3.43 (m, 1H), 2.60 (m, 2H), 2.20-2.01 (m, 6H), 1.75 (s, 3H), 1.42 (s, 9H).

Provenance & Evidence