Cesium carbonate → HCID 86601478, compound

HRID 270060Notes

Reaction equation

HRID 270060 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].[CH3:16][C@@:17]1([CH2:20]OS(C2C=CC=C([N+]([O-])=O)C=2)(=O)=O)[CH2:19][O:18]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:16][C@@:17]1([CH2:20][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:10])([F:11])[F:9])=[CH:4][C:3]=2[NH:12][C:13](=[O:15])[CH3:14])[CH2:19][O:18]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 68965568N-[2-hydroxy-5-(trifluoromethyl)phenyl]acetamideHCID 86597620HCID 86597620, compound

Product 1

HCID 86601478HCID 86601478, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-nitro-4-(trifluoromethyl)phenol (310 mg, 1.5 mmol), palladium on carbon (10%, 125 mg) and acetic anhydride (306.3 mg, 3.0 mmol) in methanol was hydrogenated for 2 h at atmospheric pressure. The catalyst was filtered off, the filtrate was concentrated in vacuo to give crude N-[2-hydroxy-5-(trifluoromethyl)phenyl]acetamide (331 mg). A part (219.16 mg, 1.0 mmol) of N-[2-hydroxy-5-(trifluoromethyl)phenyl]acetamide was treated with [(2S)-2-methyloxiran-2-yl]methyl3-nitrobenzenesulfonate (273.27 mg, 1.0 mmol) in the presence of Cs2CO3 (406.25 mg, 1.25 mmol) in DMF (5 mL) at room temperature for 5 h. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over Na2SO4, filtered, concentrated. The residue was purified by silica gel flash chromatography (0-40% ethyl acetate in petroleum ether) to give the subtitled compound (230 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-baa9c91fcf354e6db22990d7a36710ae
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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