反応式
[O:1]=[C:2]1[O:6][CH2:5][C@@H:4]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3]1.CC(C)=[O:20].C([O-])([O-])=O.[Cs+].[Cs+]>O>[OH:20][CH2:5][C@@H:4]([NH:7][C:8]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:17])[CH2:3][C:2]([OH:6])=[O:1]参加物
実験手順
In a 500 ml round-bottomed flask phenylmethyl [(3S)-5-oxotetrahydro-3-furanyl]carbamate (4.3 g, 18.28 mmol, available from Sigma-Aldrich # 419249) was dissolved in water (100 ml) and acetone (100 ml) and to this solution Cs2CO3 (10.72 g, 32.9 mmol) was added and the reaction left under stirring at room temperature for 5 hours. The solution was then transferred into a separatory funnel and washed with EtOAc (2×50 ml). The aqueous phase was then acidified to pH=2 by the addition of a 2 M HCl aqueous solution and then extracted with EtOAc (5×100 mls). The organic phase was dried (Na2SO4) and solvent removed under reduced pressure to give the title compound D1 (3.78 g) as a white solid. MS: (ES/+) m/z: 254 (M+1). C12H15NO5 requires 253. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 12.11 (bs, 1 H), 7.41-7.07 (m, 5 H), 5.17-4.92 (m, 2 H), 3.95-3.62 (m, 1 H), 3.42-3.22 (m, 2H), 2.55-2.40 (m, 1 H), 2.34-2.23 (m, 1 H).
後処理
- waitthe reaction left
- customThe solution was then transferred into a separatory funnel
- washwashed with EtOAc (2×50 ml)
- additionThe aqueous phase was then acidified to pH=2 by the addition of a 2 M HCl aqueous solution
- extractionextracted with EtOAc (5×100 mls)
- dry with materialThe organic phase was dried (Na2SO4) and solvent
- customremoved under reduced pressure
出典と根拠
- ORDレコード
- ord-e541810d00e048ceb3fa3ad3bc41bdc7
- 出典データセット
- uspto-grants-2012_03
- 特許番号
- US08133908B2
関連ノート
読み込み中…