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

HRID 1782025
ノート
印刷プレビュー

反応式

HRID 1782025 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 13387
N-methyl-2-pyrrolidone
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-114f061e04114a049b83470f3a2890ef
出典データセット
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07498338B2

反応ノート

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