Trifluoroacetic acid → HCID 68157978, compound

HRID 242949Notes

Reaction equation

HRID 242949 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([CH:15]2[CH2:18][CH2:17][CH2:16]2)[C:13]2[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][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:19]=[C:20]([F:23])[CH:21]=[CH:22][C:12]=3[N:11]=[C:10]2[C@@H:8]([NH2:7])[CH3:9])[CH2:16][CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157560HCID 68157560, compound

Product 1

HCID 68157978HCID 68157978, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-(1-cyclobutyl-6-fluoro-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester (728 mg, 2.2 mmol) in DCM (15 mL) was added TFA (8 mL) and the mixture stirred at RT for 1 h. The volatiles were removed in vacuo and the resulting residue partitioned between DCM and a saturated aqueous solution of NaHCO3. The two phase system was stirred for 10 min and the organic layer dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM) to afford the title compound as a white solid (251 mg, 49%). LCMS (Method C): RT 2.07 min [M+H]+ 234.1.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe resulting residue partitioned between DCM
  3. stirringThe two phase system was stirred for 10 min
  4. dry with materialthe organic layer dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-619c248b2cf24c0eb7c9a3b28ae25e59
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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