Cesium carbonate → HCID 86601482, compound

HRID 270077Notes

Reaction equation

HRID 270077 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[NH:12][C:13](=[O:15])[CH3:14].[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>[O:16]1[CH2:18][C@H:17]1[CH2:19][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:10])([F:11])[F:9])=[CH:4][C:3]=1[NH:12][C:13](=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 68965568N-[2-hydroxy-5-(trifluoromethyl)phenyl]acetamide

Product 1

HCID 86601482HCID 86601482, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-[2-hydroxy-5-(trifluoromethyl)phenyl]acetamide (282 mg, 1.28 mmol), (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (331.5 mg, 1.28 mmol) and Cs2CO3 (487.5 mg, 1.28 mmol) in DMF (5 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 (0-40% ethyl acetate in petroleum ether) to give the subtitled compound (150 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 (0-40% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-89e1b469872342e79e7a1125b234d2f3
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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