Water → HCID 25131532, compound

HRID 2076943Notes

Reaction equation

HRID 2076943 reaction equation
[F:1][C:2]1([F:30])[CH2:7][C@@H:6]([CH2:8][OH:9])[C@H:5]([C:10]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=3)=[CH:13][N:12]([CH2:25][C:26]([F:29])([F:28])[F:27])[N:11]=2)[CH2:4][CH2:3]1.CC(C)=[O:33].OS(O)(=O)=O.O=[Cr](=O)=O.O>CC(C)=O>[F:30][C:2]1([F:1])[CH2:7][C@@H:6]([C:8]([OH:33])=[O:9])[C@H:5]([C:10]2[C:14]([C:15]3[CH:16]=[CH:17][C:18]([S:21]([CH3:24])(=[O:22])=[O:23])=[CH:19][CH:20]=3)=[CH:13][N:12]([CH2:25][C:26]([F:29])([F:28])[F:27])[N:11]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 25131531HCID 25131531, compoundHCID 131709961Jones' reagent

Product 1

HCID 25131532HCID 25131532, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of {(1R,2R)-5,5-difluoro-2-[4-[4-(methylsulfonyl)phenyl]-1-(2,2,2-trifluoroethyl)-1H-pyrazol-3-yl]cyclohexyl}methanol (1.64 g, 3.63 mmol) in acetone (40 mL) was treated at 0° C. with Jones reagent (3.8 mL) followed by stirring at rt for 30 min. Water was added and the mixture was extracted with two portions of ethyl acetate. The combined organics were washed twice with water then with a saturated aqueous solution of NaCl before drying over Na2SO4. Concentration in vacuo gave (1R,2R)-5,5-difluoro-2-[4-[4-(methylsulfonyl)phenyl]-1-(2,2,2-trifluoroethyl)-1H-pyrazol-3-yl]cyclohexanecarboxylic acid as a faint-yellow foam.

Workup

  1. extractionthe mixture was extracted with two portions of ethyl acetate
  2. washThe combined organics were washed twice with water
  3. dry with materialwith a saturated aqueous solution of NaCl before drying over Na2SO4
  4. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-584744a4a8a54ae9976c7b36e7889b68
Source dataset
uspto-grants-2011_04
Patent number
US07928091B2

Reaction notes

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