Acetic Acid → Ammonia methanol dichloromethane
反応式
Cl.[N:2]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1.[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:49][CH:50]([Cl:52])C>>[NH3:2].[CH3:9][OH:10].[Cl:49][CH2:50][Cl:52].[CH2:23]([N:20]1[CH2:19][CH2:18][N:17]([C:14]2[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:2]3[CH2:6][CH2:5][CH2:4][CH2:3]3)=[CH:16][CH:15]=2)[CH2:22][CH2:21]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1参加物
7
反応物 5
生成物 2
実験手順
A solution of the product of Example 23 (148 mg), benzaldehyde (520 mg), and acetic acid (25 mg) in dichloroethane (3 mL) was treated with sodium triacetoxyborohydride (121 mg). After 14 h, the reaction was quenched with saturated aqueous sodium bicarbonate, and the aqueous phase was extracted with dichloromethane (120 mL). The organic phase was dried (magnesium sulfate) and evaporated in vacuo. Silica gel chromatography of the residue (5% 2M ammonia-methanol/dichloromethane) gave the title compound as a light yellow solid (8 mg). 1H NMR (400 MHz, CDCl3): 7.36-7.24 (m, 5H), 6.94-6.81 (m, 4H), 3.96 (t, J=6.4 Hz, 2H), 3.56 (s, 2H), 3.08 (t, J=4.9 Hz, 4H), 2.64-2.60 (m, 4H), 2.04-1.94 (m, 2H), 1.80-1.75 (m, 4H).
後処理
- customthe reaction was quenched with saturated aqueous sodium bicarbonate
- extractionthe aqueous phase was extracted with dichloromethane (120 mL)
- dry with materialThe organic phase was dried (magnesium sulfate)
- customevaporated in vacuo
出典と根拠
- ORDレコード
- ord-accdf9f94e824b48ab1a2eac8bb2b6b7
- 出典データセット
- uspto-grants-2008_09
- 特許番号
- US07429586B2
反応ノート
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