Cesium carbonate → N-{2-[(2S)-Oxiran-2-ylmethoxy]phenyl}acetamide

HRID 270054

反応式

HRID 270054 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:11])[CH3:10].[O:12]1[CH2:14][C@H:13]1[CH2:15]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[O:12]1[CH2:14][C@H:13]1[CH2:15][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:11])[CH3:10]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 119722-AcetamidophenolHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

生成物 1

HCID 6933328N-{2-[(2S)-Oxiran-2-ylmethoxy]phenyl}acetamide収率 64.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of N-(2-hydroxyphenyl)acetamide (1.51 g, 10 mmol), (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (2.59 g, 10 mmol) and cesium carbonate (Cs2CO3) (3.9 g, 12 mmol) in dimethylformamide (DMF) (30 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was dried over Na2SO4, filtered, concentrated and the residue was purified by silica gel flash chromatography to give the subtitled compound (1.34 g).

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and H2O
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by silica gel flash chromatography

出典と根拠

ORDレコード
ord-438c1343033a4e1aadbcfb9772f1c70f
出典データセット
uspto-grants-2008_11
特許番号
US07449475B2

関連ノート

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