Cesium carbonate → N-Cyclopropyl-4-methoxy-2-[(2S)-oxiran-2-ylmethoxy]benzamide

HRID 270066Notes

Reaction equation

HRID 270066 reaction equation
[CH:1]1([NH:4][C:5](=[O:15])[C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=2[OH:14])[CH2:3][CH2:2]1.[O:16]1[CH2:18][C@H:17]1[CH2:19]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:15])[C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=2[O:14][CH2:19][C@@H:17]2[CH2:18][O:16]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 28390698N-Cyclopropyl-2-hydroxy-4-methoxybenzamide

Product 1

HCID 71655152N-Cyclopropyl-4-methoxy-2-[(2S)-oxiran-2-ylmethoxy]benzamideYield 112.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-cyclopropyl-2-hydroxy-4-methoxybenzamide (700 mg, 3.38 mmol), (2S)-oxiran-2-ylmethyl3-nitrobenzenesulfonate (876 mg, 3.38 mmol) and Cs2CO3 (1.31 g, 4.05 mmol) in DMF (12 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 (0-80% ethyl acetate in petroleum ether) to give the subtitled compound (1.0 g).

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 (0-80% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-32b22f8d1c294a10acc538dff37e0ea4
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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