Cesium carbonate → HCID 86601485, compound

HRID 270102

Reaction equation

HRID 270102 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O.[OH:18][C:19]1[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=1[C:21]([NH:23][CH3:24])=[O:22].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:24][NH:23][C:21](=[O:22])[C:20]1[CH:25]=[CH:26][CH:27]=[CH:28][C:19]=1[O:18][CH2:4][C@@H:2]1[CH2:3][O:1]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 74624N-MethylsalicylamideHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

Product 1

HCID 86601485HCID 86601485, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (388.5 mg, 1.50 mmol), 2-hydroxy-N-methylbenzamide (226.5 mg, 1.50 mmol) and cesium carbonate (586 mg, 1.80 mmol) in dimethylformamide (6 mL) was kept on stirring at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic phase was dried over sodium sulphate, Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (0-50% ethyl acetate in petroleum ether) to give the subtitled compound (284 mg).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic phase was dried over sodium sulphate, Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash chromatography (0-50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-8b76fe2d56cc4966b0145256373f6fc8
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Linked notes

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