Water → HCID 67102144, compound

HRID 2079684Notes

Reaction equation

HRID 2079684 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[C:5]([C:9]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].S(OC)(O[CH3:27])(=O)=O.C(=O)(O)[O-].[Na+].O>CC(C)=O>[CH3:27][O:7][C:6](=[O:8])[C:5]1[C:9]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[C:4]=1[NH:16][C:17](=[O:22])[C:18]([CH3:19])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 516892Sodium BicarbonateHCID 59199292HCID 59199292, compound

Product 1

HCID 67102144HCID 67102144, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-methoxy-2-pivalamido-6-(trifluoromethyl)benzoic acid (1 eq), dimethyl sulfate (1 eq) and sodium bicarbonate (1.3 eq) in acetone was refluxed for 4 h. The reaction mixture was poured to water and extracted with ethyl acetate. The ethyl acetate extracts were combined, washed with brine and dried over sodium sulfate. Filtered, evaporated and dried under vacuum to provide product as yellow solid in 95% yield. ES/MS m/z 334.1 (MH+). Proceeds for next step without any purification.

Workup

  1. temperaturewas refluxed for 4 h
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltered
  6. customevaporated
  7. customdried under vacuum
  8. customto provide product as yellow solid in 95% yield
  9. customProceeds for next step without any purification

Sources & evidence

ORD record
ord-8e4eca5af7e04e099af44442e585b7a9
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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