Celecoxib → Methyl N-(2-Methoxy-2-oxoethl)-N-({4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}sulfonyl)glycinate

HRID 393860

Reaction equation

HRID 393860 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:14]=[CH:15][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:17][CH:18]=3)[N:11]=[C:10]([C:23]([F:26])([F:25])[F:24])[CH:9]=2)=[CH:6][CH:7]=1.Br[CH2:28][C:29]([O:31][CH3:32])=[O:30].[C:33]([O-:36])([O-])=O.[K+].[K+].[C:39]([O-])(O)=O.[Na+].CN([CH:47]=[O:48])C>>[CH3:32][O:31][C:29](=[O:30])[CH2:28][N:22]([S:19]([C:16]1[CH:15]=[CH:14][C:13]([N:12]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)=[CH:9][C:10]([C:23]([F:24])([F:26])[F:25])=[N:11]2)=[CH:18][CH:17]=1)(=[O:21])=[O:20])[CH2:39][C:33]([O:48][CH3:47])=[O:36]

Participants

6

Reactant 5

HCID 2662CelecoxibHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 516892Sodium Bicarbonate

Product 1

HCID 22647645Methyl N-(2-Methoxy-2-oxoethl)-N-({4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}sulfonyl)glycinateYield 51%

Procedure

A mixture of Celecoxib (0.500 g, 1.31 mmol), methyl bromoacetate (0.501 g, 3.28 mmol) and K2CO3 (0.362 g, 2.62 mmol) in anhydrous DMF (5.0 mL) was stirred at room temperature for 21 hours. The mixture was then poured into sat. NaHCO3 (200 mL) and extracted with ethyl acetate (200 mL). The ethyl acetate solution was then washed with sat NaCl (50 mL), dried over MgSO4, filtered and concentrated under vacuum. The crude product was purified by flash chromatography (silica gel, 98:2 methylene chloride:methanol) to afford 0.350 g (51% yield) of the product as a colorless glass: 1H NMR (dmso-d6/300 MHz) δ 7.90 (d, 2H, J=8.7 Hz), 7.53 (d, 2H, J=8.7 Hz), 7.23-7.17 (m, 5H), 4.19 (s, 4H), 3.54 (s, 6H), 2.30 (s, 31H); HRMS (M+NH4)+ calcd. for C23H26F3N4O6S: 543.1525; found: 543.1526.

Workup

  1. extractionextracted with ethyl acetate (200 mL)
  2. washThe ethyl acetate solution was then washed with sat NaCl (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by flash chromatography (silica gel, 98:2 methylene chloride:methanol)

Sources & evidence

ORD record
ord-e819c016cfd94453b1fd6abf05e5e7ab
Source dataset
uspto-grants-2004_10
Patent number
US06809111B2

Linked notes

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