Trifluoroacetic acid → HCID 178442436, compound

HRID 425388Notes

Reaction equation

HRID 425388 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-a493a55baf8943abbe6795230e424dc0
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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