Trifluoroacetic acid → HCID 178442436, compound

HRID 1881470Notes

Reaction equation

HRID 1881470 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9]([CH3:45])([CH2:43][CH3:44])[CH2:10][C:11]1[N:12]=[C:13]([CH:23]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][N:32]=3)=[CH:27][CH:26]=2)[N:14](C(OC(C)(C)C)=O)[CH:15]=1>>[CH3:8][C:9]([CH3:45])([CH2:43][CH3:44])[CH2:10][C:11]1[N:12]=[C:13]([CH:23]([NH:38][S:39]([CH3:42])(=[O:40])=[O:41])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][N:32]=3)=[CH:27][CH:26]=2)[NH:14][CH:15]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66705684tert-butyl 4-(2,2-dimethylbutyl)-2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-[(methylsulfonyl)amino]ethyl}-1H-imidazole-1-carboxylate

Product 1

HCID 178442436HCID 178442436, compound

Procedure

Trifluoroacetic acid (1 mL) was added to neat tert-butyl 4-(2,2-dimethylbutyl)-2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-[(methylsulfonyl)amino]ethyl}-1H-imidazole-1-carboxylate. After stirring at ambient temperature for 1 h, the reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and 10% aqueous sodium hydroxide. The aqueous phase was extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Preparatory plate chromatography eluting with 100% ethyl acetate afforded the title compound. (M+H) found: 445.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate and 10% aqueous sodium hydroxide
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  5. concentrationconcentrated in vacuo
  6. washPreparatory plate chromatography eluting with 100% ethyl acetate

Sources & evidence

ORD record
ord-374c53ff9cf44e1395054e5aa80c6686
Source dataset
uspto-grants-2012_11
Patent number
US08318767B2

Reaction notes

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