[BH4-].[Na+].[CH3:3][C:4]1[S:5][C:6](/[CH:18]=[CH:19]/[C:20](=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[N:8]=1.Cl>O.C(O)(C)C>[CH3:3][C:4]1[S:5][C:6](/[CH:18]=[CH:19]/[CH:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[N:8]=1The solution of 76 mg of sodium borohydride in 6 ml of water was added to the solution of 351 mg of 2-methyl-4-(6-carboxyhexyl)-5-(3-keto-1-trans-octenyl)-thiazole (Ib, R1 = CH3) in 4 ml of isopropanol. The reaction mixture was allowed to stand overnight at room temperature, then diluted with 50 ml of water, acidified with 1 N hydrochloric acid and extracted with 3 × 25 ml of ethyl acetate. The ethyl acetate extract was dried over sodium sulphate and evaporated in vacuo. The obtained 317 mg of evaporation residue was purified by preparative thin layer chromatography in the way specified in Example 6. Thus, 245 mg of 2-methyl-4-(6-carboxyhexyl)-5-(3-hydroxy-1-trans-octenyl)-thiazole (Id, R1 = CH3) were obtained. IR spectrum (film): ν OH 3500-2300, ν CH 3000-2860, ν C=O 1710, ν C=C 1640 cm -1.
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