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

HRID 270074노트

반응식

HRID 270074 반응식
[O:1]1[CH2:3][C@H:2]1[CH2:4]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:28])[CH3:27])=[C:21]([OH:29])[CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:28])[CH3:27])=[C:21]([O:29][CH2:4][C@@H:2]2[CH2:3][O:1]2)[CH:20]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 177739N-(4-Chloro-2-hydroxyphenyl)acetamide

생성물 1

HCID 86601481N-{4-Chloro-2-[(2S)-oxiran-2-ylmethoxy]phenyl}acetamide수율 73.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To a mixture of (2S)-oxiran-2ylmethyl3-nitrobenzenesulfonate (3.37 g, 13.25 mmol), N-(4-chloro-2-hydroxyphenyl)acetamide (2.46 g, 17.23 mmol) and Cs2CO3 (6.48 g, 19.88 mmol) was added DMF (20 mL) at 0° C. and the reaction mixture was stirred at 0° C. for 3 h. 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 (hexane:ethyl acetate 3:2) to give the subtitled compound (2.36 g).

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 (hexane:ethyl acetate 3:2)

출처 및 근거

ORD 기록
ord-62d08c44daf2470caad11857e41ea86f
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449475B2

반응 노트

불러오는 중…