Trifluoroacetic acid → HCID 67320897, compound

HRID 1509568Notes

Reaction equation

HRID 1509568 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 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 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. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washa fraction eluted with ethyl acetate-hexane-methanol (50:50:0-100:0:0-85:0:15)
  6. concentrationwas concentrated under reduced pressure
  7. dissolutionThe residue was dissolved in methanol (2 ml)
  8. additionfumaric acid (15 mg) was added
  9. stirringthe mixture was stirred at room temperature for 1 hr
  10. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6bb3a59575694eb3938817f201bcb5b2
Source dataset
uspto-grants-2015_12
Patent number
US09221836B2

Reaction notes

Loading…