Hydrochloric Acid → {(3S)-1-[5-(adamantan-1-ylcarbamoyl)-6-(propylthio)pyridin-2-yl]piperidin-3-yl}acetic acid
反応式
[OH-].[Li+].[C:3]12([NH:13][C:14]([C:16]3[CH:17]=[CH:18][C:19]([N:26]4[CH2:31][CH2:30][CH2:29][C@@H:28]([CH2:32][C:33]([O:35]C)=[O:34])[CH2:27]4)=[N:20][C:21]=3[S:22][CH2:23][CH2:24][CH3:25])=[O:15])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.Cl>O.CO.C1COCC1.CCOC(C)=O>[C:3]12([NH:13][C:14]([C:16]3[CH:17]=[CH:18][C:19]([N:26]4[CH2:31][CH2:30][CH2:29][C@@H:28]([CH2:32][C:33]([OH:35])=[O:34])[CH2:27]4)=[N:20][C:21]=3[S:22][CH2:23][CH2:24][CH3:25])=[O:15])[CH2:12][CH:7]3[CH2:6][CH:5]([CH2:11][CH:9]([CH2:8]3)[CH2:10]1)[CH2:4]2参加物
反応物 3
生成物 1
試薬・触媒・溶媒 4
反応条件
- 温度
- 18 °C
実験手順
A solution of lithium hydroxide (0.053 g, 1.26 mmol) in water (1 mL) was added dropwise to a stirred solution of methyl {(3S)-1-[5-(adamantan-1-ylcarbamoyl)-6-(propylthio)pyridin-2-yl]piperidin-3-yl}acetate (Intermediate 73, 204 mg, 0.42 mmol) in MeOH (3 mL) and THF (2 mL) at 18° C., over a period of 1 minute. The resulting solution was stirred at 18° C. for 20 hours. The reaction mixture was adjusted to pH 4.5 with 2M HCl and the reaction mixture was diluted with EtOAc (50 mL), and washed sequentially with water (20 mL) and saturated brine (20 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford {(3S)-1-[5-(adamantan-1-ylcarbamoyl)-6-(propylthio)pyridin-2-yl]piperidin-3-yl}acetic acid (180 mg, 91%), as a white solid.
後処理
- washwashed sequentially with water (20 mL) and saturated brine (20 mL)
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- customevaporated
出典と根拠
- ORDレコード
- ord-1c3f933cce244ab499cefebb3ed84625
- 出典データセット
- uspto-grants-2011_06
- 特許番号
- US07964618B2
反応ノート
読み込み中…