Diisopropylethylamine → 2(S)-Benzyloxycarbonylamino-3-(2-benzyloxy-5-iodophenyl)propionic acid

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Reaction Steps

9.25 ml (53.09 mol) of N,N-diisopropylethylamine are added to a solution of 10.46 g (24.13 mmol) of 2(S)-amino-3-(2-benzyloxy-5-iodophenyl)propionic acid hydrochloride (Example 9A) in DMF. 6.615 g (26.54 mmol) of N-(benzyloxycarbonyl)succinimide (Z-OSuc) are added thereto. The resulting solution is stirred overnight and then concentrated on a rotary evaporator in vacuo. The residue is taken up in dichloromethane and extracted twice each with a 0.1N hydrochloric acid solution and a saturated aqueous sodium chloride solution. The organic phase is dried, filtered and concentrated. The mixture is purified by column chromatography on silica gel (mobile phase: cyclohexane/diethyl ether 9:1 to 8:2).

Provenance & Evidence