反応式
C([BH3-])#N.[Na+].Cl.[F:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH2:16][CH:17]2[CH2:20][NH:19][CH2:18]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1.[F:21][C:22]1[CH:32]=[CH:31][C:25]2[C:26]([CH:29]=O)=[CH:27][S:28][C:24]=2[CH:23]=1>CO.C(O)(=O)C>[F:21][C:22]1[CH:32]=[CH:31][C:25]2[C:26]([CH2:29][N:19]3[CH2:20][CH:17]([CH2:16][S:13]([C:10]4[CH:11]=[CH:12][C:7]([F:6])=[CH:8][CH:9]=4)(=[O:15])=[O:14])[CH2:18]3)=[CH:27][S:28][C:24]=2[CH:23]=1参加物
反応物 3
生成物 1
試薬・触媒・溶媒 2
実験手順
Sodium cyanoborohydride (13 mg, 0.20 mmol) was added to a stirred solution of 3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine hydrochloride (Example 1 Step 4, 49 mg, 0.18 mmol) and 6-fluoro-1-benzothiophene-3-carbaldehyde (36 mg, 0.20 mmol) in methanol (3 mL) and acetic acid (50 μL). The reaction was stirred at room temperature for 4 hours. The solvent was removed in vacuo and the residue partitioned between sodium carbonate and ethyl acetate. The aqueous layer was extracted with further ethyl acetate and the combined organic layers washed with water and brine, dried over MgSO4 and evaporated. The residue was purified by preparative TLC (40% ethyl acetate/isohexane) to give the title compound which was treated with ethereal HCl to give the hydrochloride salt (46 mg, 59%). 1H NMR (400 MHz, CD3OD) δ 8.00–7.96 (3H, m), 7.88 (1H, s), 7.74 (1H, dd, J=2.4, 8.8 Hz), 7.43–7.37 (2H, m), 7.31–7.27 (1H, m), 4.68 (2H, s), 4.24 (2H, s), 4.16 (2H, t, J=9.7 Hz), 3.67 (2H, d, J=7.6 Hz), 3.30–3.22 (1H, m); m/z (ES+) 394 (M+H)+.
後処理
- customThe solvent was removed in vacuo
- customthe residue partitioned between sodium carbonate and ethyl acetate
- extractionThe aqueous layer was extracted with further ethyl acetate
- washthe combined organic layers washed with water and brine
- dry with materialdried over MgSO4
- customevaporated
- customThe residue was purified by preparative TLC (40% ethyl acetate/isohexane)
出典と根拠
- ORDレコード
- ord-f183d92f09df40309c2cbbef87d5eb4a
- 出典データセット
- uspto-grants-2006_08
- 特許番号
- US07094777B2
関連ノート
読み込み中…