Lithium Hydroxide → (4s,5r)-3-benzoyl-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid

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Reaction Steps

(4S-trans)-3-Benzoyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid, ethyl ester (1.56 g) was dissolved in THF (10 ml) at room temperature and LiOH (4.63 ml, 1M in H2O) was added dropwise. Initially, a bi-phasic mixture was observed, but after the addition of the last quantity of LiOH and stirring for 5 minutes the solution became homogeneous. After further stirring for ½ hour, the reaction mixture was quenched with aqueous 1N HCl (4.63 ml), and diluted with EtOAc and saturated NaCl. The H2O layer (pH=3) was twice extracted with EtOAc, and the combined organic phase dried with MgSO4. The solvent was removed in vacuo to give 1.39 g of the title product acid (97%) which was homogeneous by TLC and 1H NMR.

Provenance & Evidence