Hydrochloric Acid → cis4-hydroxy-N-benzyloxycarbonyl-D-proline 2-oxo-1,2-diphenylethyl ester

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Reaction Steps

To a solution of cis-4-(tert-butyldimethylsilyloxy)-N-benzyloxycarbonyl-D-proline 2-oxo-1,2-diphenylethyl ester (21.62 g) in MeOH-THF (2:1, 380 mL) was added 1N HCl (76 mL) at 5° C., and the mixture was stirred at room temperature for 24 hours. To the reaction mixture was added NaHCO3 (6.7 g) at 5° C. The organic solvent was evaporated, and the residue was extracted with EtOAc. The organic layer was washed with water and brine, dried (MgSO4), and evaporated in vacuo. The residue was purified by silica gal column chromatography (hexane-EtOAc, 2:1˜1:3 elution) to give cis4-hydroxy-N-benzyloxycarbonyl-D-proline 2-oxo-1,2-diphenylethyl ester (13.90 g).

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