Cesium carbonate → N-{5-Chloro-2-[(2S)-oxiran-2-ylmethoxy]phenyl}acetamide

HRID 270072

반응식

HRID 270072 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=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>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:16][C@@H:14]2[CH2:15][O:13]2)=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 952582-Acetylamino-4-chlorophenolHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

생성물 1

HCID 86601480N-{5-Chloro-2-[(2S)-oxiran-2-ylmethoxy]phenyl}acetamide수율 92.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of N-(5-chloro-2-hydroxyphenyl)acetamide (500 mg, 2.69 mmol), (2S)-oxiran-2-ylmethyl3-nitrobenzenesulfonate (697 mg, 2.69 mmol) and Cs2CO3 (1.04 g, 3.22 mmol) in DMF (10 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (0-50% ethyl acetate in petroleum ether) to give the subtitled compound (600 mg).

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash chromatography (0-50% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-ba1e445f47844faaa2ea1eba40902c38
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449475B2

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