Trifluoroacetic acid → HCID 178461857, compound

HRID 243087Notes

Reaction equation

HRID 243087 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([C@H:15]2[CH2:18][C@H:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16]2)[C:13]2[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:12]=2[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:20]([O:19][C@H:17]1[CH2:18][C@H:15]([N:14]2[C:13]3[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:12]=3[N:11]=[C:10]2[C@@H:8]([NH2:7])[CH3:9])[CH2:16]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178462194HCID 178462194, compound

Product 1

HCID 178461857HCID 178461857, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-[1-(trans-3-benzyloxycyclobutyl)-6-fluoro-1H-benzoimidazol-2-yl]ethyl]carbamic acid tert-butyl ester (0.46 g, 1.05 mmol) in DCM (10 mL) was added TFA (4 mL) and the mixture stirred at RT for 1 h. The volatiles were removed in vacuo and the resulting pale red gummy residue dissolved in DCM and loaded onto an SCX-2 (20 g) cartridge. The cartridge washed with DCM then MeOH and then 2M NH3 in MeOH solution. The relevant fractions were concentrated in vacuo to afford the title compound as yellow gum (0.28 g, 80%). LCMS (Method B): RT 2.17 min [M+H]+ 340

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe resulting pale red gummy residue dissolved in DCM
  3. washThe cartridge washed with DCM
  4. concentrationThe relevant fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-520f9da7e8e6422f8ef115afc11d2688
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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