Cesium carbonate → N-{4-Fluoro-2-[(2S)-oxiran-2-ylmethoxy]phenyl}acetamide

HRID 270056

반응식

HRID 270056 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([OH:12])[CH:3]=1.[O:13]1[CH2:15][C@H:14]1[CH2:16]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([O:12][CH2:16][C@@H:14]2[CH2:15][O:13]2)[CH:3]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 177738N-(4-fluoro-2-hydroxyphenyl)acetamide

생성물 1

HCID 20806548N-{4-Fluoro-2-[(2S)-oxiran-2-ylmethoxy]phenyl}acetamide수율 59.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of N-(4-fluoro-2-hydroxyphenyl)acetamide (1.69 g, 10.0 mmol), (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (2.59 g, 10.0 mmol) and Cs2CO3 (4.87 g, 15.0 mmol) in DMF (15 mL) was stirred at room temperature for 2 h. The reaction mixture was partitioned between ethylacetate and H2O. The organic layer was dried over Na2SO4 filtered and concentrated. The residue was purified by silica gel flash chromatography to give the subtitled compound (1.35 g).

후처리

  1. customThe reaction mixture was partitioned between ethylacetate 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-c2a74e928c0541fabba85367338fbe14
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449475B2

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