Hydrochloric Acid → 2-(4-(((Benzyloxy)carbonyl)amino)phenoxy)acetic acid

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Reaction Steps

1.67 ml (1.67 mmol) of a 1N aqueous solution of sodium hydroxide were added, whilst ice-cooling, to a solution of 500 mg (1.52 mmol) of ethyl 4-(benzyloxycarbonylamino)phenoxyacetate (prepared as described in Preparation 14) in 10 ml of methanol, and the mixture was stirred at room temperature for 1 hour. At the end of this time, the reaction mixture was neutralized by the addition of 1N aqueous hydrochloric acid, and the solvent was removed by distillation under reduced pressure. The residue was diluted with ethyl acetate, and the resulting organic solution was washed with a 5% w/v aqueous solution of citric acid and with a saturated aqueous solution of sodium chloride, in that order. The reaction mixture was then dried over sodium sulfate, and the organic solvent was removed by distillation under reduced pressure. The concentrate was triturated with diethyl ether, to give 417 mg of the title compound as colorless crystals, melting at 152°-154° C.

Provenance & Evidence