O.[OH-].[Li+].OO.C([C@@H]1COC(=O)N1[C:19]([CH:21]1[CH2:25][C:24](=[O:26])[N:23]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=2[O:36][CH3:37])[CH2:22]1)=[O:20])C1C=CC=CC=1.S([O-])(O)=[O:39].[Na+]>O.O1CCCC1>[CH3:37][O:36][C:29]1[CH:30]=[C:31]([O:34][CH3:35])[CH:32]=[CH:33][C:28]=1[CH2:27][N:23]1[C:24](=[O:26])[CH2:25][CH:21]([C:19]([OH:20])=[O:39])[CH2:22]1To a solution of lithium hydroxide monohydrate (3.29 g) in water (50 ml) was added dropwise 30 wt % aqueous solution of hydrogen peroxide (17.5 ml) under cooling with an ice-sodium chloride bath, and the mixture was stirred for 15 minutes. To this reaction solution was added tetrahydrofuran (30 ml), and then a solution of the low-polarity component of (R)-4-benzyl-3-[1-(2,4-dimethoxybenzyl)-5-oxopyrrolidine-3-carbonyl]-2-oxazolidinone (26.4 g) in tetrahydrofuran (150 ml) was added dropwise thereto, and the mixture was stirred for additional 1 hour. To this reaction solution was slowly added a solution of sodium hydrogen sulfite (18.7 g) in water (60 ml), and the mixture was warmed to room temperature by removing the bath, and then extracted with ethyl acetate (100 ml). The resulting organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform/ethyl acetate=1/1 to 1/2, chloroform/methanol=5/1) to give the titled compound (14.3 g). An analysis of this solid by HPLC analysis condition 2 showed that an isomer with shorter retention time was a main product.
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