Lithium hydroxide, monohydrate → ((S)-1-{hydroxy-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazol-2-yl]-methyl}-propyl)-carbamic acid tert-butyl ester

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Reaction Steps

Acetic acid (S)-2-tert-butoxycarbonylamino-1-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazol-2-yl]-butyl ester (0.61 mmol, 0.28 g) is dissolved in a mixture of THF (10 mL) and water (10 mL). Lithium hydroxide hydrate (1.22 mmol, 0.051 g) is added and the reaction mixture stirred for 2 h. The solvents are evaporated under reduced pressure and the residue transferred into a separating funnel with 300 mL ethyl acetate and 50 mL water. The phases are separated and the organic phase washed with brine (100 mL). The organic phase is then dried with magnesium sulfate. The solvent is evaporated under reduced pressure and dried under high vacuum to yield ((S)-1-{hydroxy-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazol-2-yl]-methyl}-propyl)-carbamic acid tert-butyl ester as an oil (0.225 g, 89%) MS: m/z=440 (M+Na+), 418 (M+H+)

Provenance & Evidence