Trifluoroacetic acid → HCID 68157781, compound

HRID 243137Notes

Reaction equation

HRID 243137 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[C:13]2[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:12]=2[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:15]1([N:14]2[C:13]3[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:12]=3[N:11]=[C:10]2[C@@H:8]([NH2:7])[CH3:9])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68179456HCID 68179456, compound

Product 1

HCID 68157781HCID 68157781, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[(S)-1-[1-Cyclohexyl-6-fluoro-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester (0.55 g, 1.52 mmol) was dissolved in DCM (10 mL) and TFA (4 mL) added. The reaction mixture was stirred at RT for 30 minutes. The resultant mixture was concentrated in vacuo and the residue was dissolved in DCM (40 mL) and stirred vigorously with saturated aqueous NaHCO3 for 10 minutes. The layers were separated and the organic fraction was washed with brine (20 mL), dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a dark yellow gum which solidified on standing (0.41 g, 100%). 1H NMR (CDCl3, 400 MHz): δ 7.63 (1H, s), 7.22 (1H, s), 7.01-6.89 (1H, m), 4.43-4.21 (2H, m), 2.29-2.09 (2H, m), 2.06-1.66 (5H, m), 1.57 (3H, s), 1.51-1.23 (3H, m)

Workup

  1. concentrationThe resultant mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in DCM (40 mL)
  3. stirringstirred vigorously with saturated aqueous NaHCO3 for 10 minutes
  4. customThe layers were separated
  5. washthe organic fraction was washed with brine (20 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-553de182ecb440f18c0bc0252df8d4ce
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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