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

HRID 270054

반응식

HRID 270054 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-438c1343033a4e1aadbcfb9772f1c70f
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449475B2

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