Sodium Hydroxide → 3-Allyloxycarbonylamino-4-oxo-5-phenyl-pentanoic acid tert-butyl ester

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Reaction Steps

A solution of 3-allyloxycarbonylamino-4-hydroxy-5-phenyl-pentanoic acid tert-butyl ester, 107, (0.8 g, 2.23 mmol) in CH2Cl2 (10 mL) is added to a solution of Dess-Martin reagent (1.05 g, 2.47 mmol) in CH2Cl2 (10 mL). After 1 hour the reaction solution is diluted with ether (50 mL) and the solution poured into a 1.3 M solution of NaOH (20 mL). Stir for 1 hour and decant the organic layer. Dry the organic layer over Na2SO4, concentrate in vacuo to afford a crude residue that is purified over silica to afford the desired product.

Provenance & Evidence