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

HRID 1782025
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HRID 1782025 반응식
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([NH:11][CH3:12])=[O:10].[N+](C1C=C(S(O[CH2:26][C@@H:27]2[CH2:29][O:28]2)(=O)=O)C=CC=1)([O-])=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O.O>[CH3:12][NH:11][C:9](=[O:10])[CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][CH2:26][C@@H:27]1[CH2:29][O:28]1
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참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 217123112-(2-hydroxyphenyl)-N-methylacetamide

생성물 1

HCID 86612852N-Methyl-2-{2-[(2S)-oxiran-2-ylmethoxy]phenyl}acetamide수율 28.9%

시약·촉매·용매 2

HCID 962Water용매
HCID 13387
N-methyl-2-pyrrolidone
용매

실험 절차

A mixture of 2-(2-hydroxyphenyl)-N-methylacetamide (1.00 g, 6.1 mmol) prepared according to a known procedure (Bernd, Peschke, Eur. J. Med. Chem., 2000, 35, 599-618), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (1.58 g, 6.1 mmol) and cesium carbonate (2.37 g, 7.3 mmol) in 1-methylpyrrolidin-2-one (15 ml) was stirred at room temperature overnight. The mixture was diluted with water and extracted with ethyl acetate, the combined organic layers were dried with sodium sulphate, volatiles were removed in vacuo. The residue was purified by recrystillaziation from ethyl acetate/heptane; (390 mg) of the subtitle compound was obtained.

후처리

  1. customprepared
  2. extractionextracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried with sodium sulphate, volatiles
  4. customwere removed in vacuo
  5. customThe residue was purified by recrystillaziation from ethyl acetate/heptane

출처 및 근거

ORD 기록
ord-114f061e04114a049b83470f3a2890ef
출처 데이터셋
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07498338B2

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