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

HRID 1782025Notes

Reaction equation

HRID 1782025 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-114f061e04114a049b83470f3a2890ef
Source dataset
uspto-grants-2009_03
Patent number
US07498338B2

Reaction notes

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