Methanol → 4-[5-(2-Methylsulfonylpyrimidin-4-yl)-4-(3-trifluoromethylphenyl)-1H-imidazol-2-yl]piperidine-1-carboxylic acid benzyl ester

HRID 342690Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 342690
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[NH:18][C:19]([C:32]3[CH:37]=[CH:36][N:35]=[C:34](SC)[N:33]=3)=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)[N:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[O:41][S:42]([O-:44])=O.[K+].[CH3:46]O>>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]2[NH:18][C:19]([C:32]3[CH:37]=[CH:36][N:35]=[C:34]([S:42]([CH3:46])(=[O:44])=[O:41])[N:33]=3)=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:30])([F:31])[F:29])[CH:23]=3)[N:21]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 106503634-[5-(2-Methylthiopyrimidin-4-yl)-4-(3-trifluoromethylphenyl)-1H-imidazol-2-yl]piperidine-1-carboxylic acid benzyl esterHCID 23707502Potassium hydroxy sulfite

Produkt 1

HCID 106748344-[5-(2-Methylsulfonylpyrimidin-4-yl)-4-(3-trifluoromethylphenyl)-1H-imidazol-2-yl]piperidine-1-carboxylic acid benzyl ester

Versuchsvorschrift

To a stirring solution of 4-[5-(2-methylthiopyrimidin-4-yl)-4-(3-trifluoromethylphenyl)-1H-imidazol-2-yl]piperidine-1-carboxylic acid benzyl ester (2.5 g, 0.0045 mole) in methanol (75 mL) at 20° C. was slowly added an aqueous solution (75 mL) of Oxone® (8.32 g, 0.0135 mole). The reaction was allowed to stir for 4 hours, concentrated in vacuo to remove methanol, diluted with 10% aqueous sodium bicarbonate (100 mL), and extracted with ethyl acetate (2×150 mL). The organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound (2.75 g).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customto remove methanol
  3. additiondiluted with 10% aqueous sodium bicarbonate (100 mL)
  4. extractionextracted with ethyl acetate (2×150 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d80a8e25ece74187a956e4b5814a0bf2
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859041

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