Trifluoroacetic acid → HCID 178442463, compound

HRID 425380Notes

Reaction equation

HRID 425380 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:15][CH:16]([C:36]1[N:37](C(OC(C)(C)C)=O)[CH:38]=[C:39]([CH2:41][C:42]([CH3:46])([CH3:45])[CH2:43][CH3:44])[N:40]=1)[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:25]=[N:26][N:27](C(OC(C)(C)C)=O)[CH:28]=2)=[CH:20][CH:19]=1)=O)(C)(C)C>>[CH3:45][C:42]([CH3:46])([CH2:43][CH3:44])[CH2:41][C:39]1[N:40]=[C:36]([CH:16]([NH2:15])[CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[CH:28]=[N:27][NH:26][CH:25]=3)=[CH:22][CH:23]=2)[NH:37][CH:38]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66705673tert-butyl 4-(4-{2-[(tert-butoxycarbonyl)amino]-2-[1-(tert-butoxycarbonyl)-4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]ethyl}phenyl)-1H-pyrazole-1-carboxylate

Product 1

HCID 178442463HCID 178442463, compound

Procedure

Trifluoroacetic acid (2 mL) was added to neat tert-butyl 4-(4-{2-[(tert-butoxycarbonyl)amino]-2-[1-(tert-butoxycarbonyl)-4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]ethyl}phenyl)-1H-pyrazole-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 to afford the title compound. (M+H) found: 338.

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

Sources & evidence

ORD record
ord-5662f04865684710ae08ee17a42c25e2
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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