Cesium carbonate → HCID 71655151, compound

HRID 270062Notes

Reaction equation

HRID 270062 reaction equation
[CH:1]1([NH:4][C:5](=[O:13])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[OH:12])[CH2:3][CH2:2]1.[O:14]1[CH2:16][C@H:15]1[CH2:17]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH:1]1([NH:4][C:5](=[O:13])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:12][CH2:17][C@@H:15]2[CH2:16][O:14]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 822771N-cyclopropyl-2-hydroxybenzamide

Product 1

HCID 71655151HCID 71655151, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-cyclopropyl-2-hydroxybenzamide (270 mg, 1.52 mmol), (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (378 mg, 1.68 mmol) and cesium carbonate (645 mg, 1.98 mmol) in DMF (4 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (40% heptane in ethyl acetate) to give the subtitled compound (354 mg).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash chromatography (40% heptane in ethyl acetate)

Sources & evidence

ORD record
ord-d7172f05f22044dab62ef945d38fd137
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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