Water → Celecoxib Carboxylic Acid

HRID 966443Notes

Reaction equation

HRID 966443 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=3)[N:12]=[C:11]([C:24]([F:27])([F:26])[F:25])[CH:10]=2)=[CH:5][CH:4]=1.CC(C)=[O:30].OS(O)(=O)=O.O=[Cr](=O)=O.C(OCC)(=O)C.O>CC(C)=O>[NH2:23][S:20]([C:17]1[CH:16]=[CH:15][C:14]([N:13]2[C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([OH:30])=[O:1])=[CH:8][CH:7]=3)=[CH:10][C:11]([C:24]([F:25])([F:26])[F:27])=[N:12]2)=[CH:19][CH:18]=1)(=[O:22])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 99087764'-HydroxycelecoxibHCID 131709961Jones' reagent

Product 1

HCID 10047220Celecoxib Carboxylic Acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To the product from Example 11 in 2 mL of acetone was added 1.33 M Jones reagent until an orange color persisted. The reaction was poured into 20 mL of ethyl acetate and 20 mL of H2O and the organic layer separated, washed with saturated sodium bisulfite and dried over MgSO4. The crude product was filtered through silica gel/Celite to afford the title compound as a yellow solid: HRMS m/z 411.0507 (calc'd for C17H12N3O4SF3, 411.0500).

Workup

  1. customthe organic layer separated
  2. washwashed with saturated sodium bisulfite
  3. dry with materialdried over MgSO4
  4. filtrationThe crude product was filtered through silica gel/Celite

Sources & evidence

ORD record
ord-2dbcf1a02e3241a295f6c2c35e9fa91b
Source dataset
uspto-grants-2005_10
Patent number
US06951949B2

Reaction notes

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