Trifluoroacetic acid → HCID 67320897, compound

HRID 1184234Notes

Reaction equation

HRID 1184234 reaction equation
[CH3:1][O:2][C:3]1[N:4]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:5]([CH2:36][CH2:37][CH2:38][CH2:39][O:40][CH3:41])=[C:6]([C:8]([N:10]([CH2:32][CH:33]([CH3:35])[CH3:34])[C@H:11]2[CH2:16][C@@H:15]([C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[O:18])[CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]2)=[O:9])[N:7]=1.[C:48](=[O:51])([O-:50])[O-].[K+].[K+].FC(F)(F)C(O)=[O:57]>>[C:39]([OH:40])(=[O:57])/[CH:38]=[CH:37]/[C:48]([OH:50])=[O:51].[CH3:1][O:2][C:3]1[N:4]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:5]([CH2:36][CH2:37][CH2:38][CH2:39][O:40][CH3:41])=[C:6]([C:8]([N:10]([CH2:32][CH:33]([CH3:35])[CH3:34])[C@H:11]2[CH2:16][C@@H:15]([C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[O:18])[CH2:14][NH:13][CH2:12]2)=[O:9])[N:7]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 58355442HCID 58355442, compound

Product 1

HCID 67320897HCID 67320897, compound

Procedure

tert-Butyl(3S,5R)-3-[{[2-methoxy-5-(4-methoxybutyl)-1-phenyl-1H-imidazol-4-yl]carbonyl}(2-methylpropyl)amino]-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate (110 mg) was dissolved in trifluoroacetic acid (25% toluene solution, 4 ml), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was basified with saturated aqueous potassium carbonate solution, and extracted with ethyl acetate. The m extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane-methanol (50:50:0-100:0:0-85:0:15) was Is concentrated under reduced pressure. The residue was dissolved in methanol (2 ml), fumaric acid (15 mg) was added and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure to give the object product (86 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe m extract
  3. washwas washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washa fraction eluted with ethyl acetate-hexane-methanol (50:50:0-100:0:0-85:0:15)
  7. concentrationwas Is concentrated under reduced pressure
  8. dissolutionThe residue was dissolved in methanol (2 ml)
  9. additionfumaric acid (15 mg) was added
  10. stirringthe mixture was stirred at room temperature for 1 hr
  11. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-42c27ed697fc4d26aab1138a31dcb708
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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