Water → Celecoxib Carboxylic Acid

HRID 2298386Notes

Reaction equation

HRID 2298386 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 m of H2O and the organic layer separated, washed with saturated sodium bisulfite and dried over MgSO4. The crude was 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. filtrationwas filtered through silica gel/Celite

Sources & evidence

ORD record
ord-60e5533c91dc4122ab808c447d7bde1c
Source dataset
uspto-grants-2002_12
Patent number
US06492411B1

Reaction notes

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