Hydrochloric Acid → (3S)-1-t-Butoxycarbonyl-3-hydroxy-N-t-butyl-L-prolinamide

Participants

Reaction Conditions

Reaction Steps

0.17 ml (0.17 mmol) of a 1N aqueous solution of sodium hydroxide was added, whilst ice-cooling, to a solution of 63 mg (0.16 mmol) of (3S)-1-t-butoxycarbonyl-3-benzoyloxy-N-t-butyl-L-prolinamide [prepared as described in step (c) above] in 1 ml of methanol and the mixture was stirred at 0° C. for 30 minutes. At the end of this time, the reaction mixture was neutralized with 1N aqueous hydrochloric acid, and the solvent was removed by distillation under reduced pressure. The resulting residue was diluted with ethyl acetate. The ethyl acetate solution was washed with a 5% w/v aqueous solution of citric acid, with a 5% aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order. The reaction mixture was then dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 36 mg of the title compound as colorless crystals, melting at 122°-124° C.

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