Cesium carbonate → Methyl 4-(acetylamino)-3-[(2S)-oxiran-2-ylmethoxy]benzoate

HRID 270125Notes

Reaction equation

HRID 270125 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[OH:15])(=[O:3])[CH3:2].[N+](C1C=C(S(O[CH2:29][C@@H:30]2[CH2:32][O:31]2)(=O)=O)C=CC=1)([O-])=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[O:15][CH2:29][C@@H:30]1[CH2:32][O:31]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 22627408Methyl 4-acetamido-3-hydroxybenzoate

Product 1

HCID 86601491Methyl 4-(acetylamino)-3-[(2S)-oxiran-2-ylmethoxy]benzoateYield 36.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 4-(acetylamino)-3-hydroxybenzoate (0.209 g, 1 mmol), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (0.26 g, 1 mmol) and caesium carbonate (0.39 g, 1.2 mmol) in dimethylformamide (5 mL) was stirred at room temperature overnight. The mixture was partitioned between water and ethyl acetate, and the organic phase was washed twice with water and once with brine, and finally concentrated. The crude material was purified by flash chromatoghrphy on silica gel (eluent:ethyl acetate/n-heptane), yielding the subtitle compound (96 mg, 36%) as colourless oil.

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. washthe organic phase was washed twice with water and once with brine
  3. concentrationfinally concentrated
  4. customThe crude material was purified by flash chromatoghrphy on silica gel (eluent:ethyl acetate/n-heptane)

Sources & evidence

ORD record
ord-02d429e219a14713b0e3fe35a608ee24
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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