[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:17][CH2:18][C:19]([O:21]C)=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(#N)C.[OH-].[Li+].C(O)(=O)C>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:17][CH2:18][C:19]([OH:21])=[O:20])(=[O:9])=[O:10])=[CH:4][CH:3]=1A mixture of 3046 g of methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-propyl]octanoate, 10 L of acetonitrile and 6701 mL of 2M lithium hydroxide is stirred at room temperature overnight, and then diluted with 20 L of water. Acetic acid (1 L) is added to adjust pH to 5.5 and additional water (12 L) is added. The precipitated product is collected and resuspended in 50 L of water. The suspension is stirred, the precipitate is collected, washed with water and dried at 60°/3 mm Hg for 48 hours. The product is recrystallized twice from ethyl acetate and once from acetonitrile to yield 8-(p-chlorophenylsulfonamido)4-[3-(3-pyridyl)-propyl]-octanoic acid, m.p. 116.5-118°.
読み込み中…