Sodium Bicarbonate → N-Benzyl-N-[2-benzyloxy-5-(2-bromoacetyl)phenyl]methanesulfonamide
反応式
[Br-:1].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[C:34]([C:37]1[CH:38]=[CH:39][C:40]([O:55][CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)=[C:41]([N:43]([CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[S:44]([CH3:47])(=[O:46])=[O:45])[CH:42]=1)(=[O:36])[CH3:35].C(=O)(O)[O-].[Na+]>C1COCC1>[CH2:48]([N:43]([C:41]1[CH:42]=[C:37]([C:34](=[O:36])[CH2:35][Br:1])[CH:38]=[CH:39][C:40]=1[O:55][CH2:56][C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1)[S:44]([CH3:47])(=[O:46])=[O:45])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1参加物
実験手順
Phenyltrimethylammonium tribromide (1.19 g, 3.16 mmol) was added to a solution of N-(5-acetyl-2-benzyloxyphenyl)-N-benzylmethanesulfonamide (32) (1.23 g, 3.01 mmol) in anhydrous THF (15 mL) in three portions. The reaction mixture was stirred at rt for 16 h. An aqueous sodium bicarbonate solution (5%, 15 mL) was then added. The mixture was extracted with dichloromethane and combined organics were concentrated by rotary evaporation. The resulting residue was purified by Biotage silica gel column chromatography eluting with dichloromethane to give bromo ketone 33 as a solid (1.25 g, 85% yield): 1H NMR (500 MHz, CDCl3) δ 2.85 (s, 3H), 4.21 (s, 2H), 4.75 (br, 2H), 5.19 (s, 2H), 7.08 (d, 1H), 7.22 (m, 5H), 7.43 (m, 5H), 7.65 (d, 1H), 7.92 (dd, 1H).
後処理
- extractionThe mixture was extracted with dichloromethane
- concentrationcombined organics were concentrated by rotary evaporation
- customThe resulting residue was purified by Biotage silica gel column chromatography
- washeluting with dichloromethane
出典と根拠
- ORDレコード
- ord-9879d8b0080e468983b71eab37cd290a
- 出典データセット
- uspto-grants-2012_04
- 特許番号
- US08163758B2
反応ノート
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