[BH4-].[Na+].C(O)(=O)C(C(C(O)=O)O)O.[O:13]1[CH2:17][CH2:16][O:15][CH:14]1[C:18]1[S:19][C:20]([C:23](=[O:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:21][N:22]=1>O1CCCC1>[O:15]1[CH2:16][CH2:17][O:13][CH:14]1[C:18]1[S:19][C:20]([CH:23]([OH:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:21][N:22]=1A suspension of sodium borohydride (6.18 g) and DL-tartaric acid (24.5 g) in tetrahydrofuran (250 mL) was stirred at 80° C. for 2 hr. The reaction mixture was cooled to 0° C., ethyl [2-(1,3-dioxolan-2-yl)-1,3-thiazol-5-yl](oxo)acetate (10.49 g) was added, and the mixture was stirred at room temperature for 2 days. The reaction mixture was slowly poured into ice (100 g), and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO9) and concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (8.43 g, yield 80%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (4:1, volume ratio). MS: 260 (MH+).
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