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

HRID 1166285

Reaktionsgleichung

Reaktionsgleichung von HRID 1166285
[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]

Komponenten

6

Edukt 5

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

Produkt 1

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

Versuchsvorschrift

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, 3H); HRMS (M+NH4)+ calcd. for C23H26F3N4O6S: 543.1525; found: 543.1526.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-c87862b54a0247bcb2a4b8c011a2bb06
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613790B2

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