Lithium Hydroxide → N-[(S)-5-(2-Benzyloxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-2,2-dimethyl-malonamic acid

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Reaction Steps

N—[(S)-5-(2-Benzyloxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-2,2-dimethyl-malonamic acid ethyl ester (127 mg, 0.25 mmol) were dissolved in THF (4.5 ml) and water (1.1 ml), treated with lithium hydroxide (25 mg, 1 mmol) and stirred for 18 h at ambient temperature. The mixture is diluted with aqueous saturated sodium carbonate and extracted twice with ethyl acetate. The aqueous phase is acidified with concentrated aqueous hydrogen chloride to pH 0 and extracted twice with ethyl acetate. The acidic organic layers were combined, dried over magnesium sulfate and evaporated to afford 112 mg (93%) of white foam. MS: m/e=472(M−H+).

Provenance & Evidence