Trifluoroacetic acid → HCID 58459300, compound

HRID 242953Notes

Reaction equation

HRID 242953 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([CH:15]2[CH2:17][CH2:16]2)[C:13]2[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][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:18]=[C:19]([F:22])[CH:20]=[CH:21][C:12]=3[N:11]=[C:10]2[C@@H:8]([NH2:7])[CH3:9])[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67433192HCID 67433192, compound

Product 1

HCID 58459300HCID 58459300, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-(1-cyclopropyl-6-fluoro-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester (414 mg, 1.3 mmol) in DCM (7 mL) was added TFA (3 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 then the organic layer was 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 yellow oil (166 mg, 58%). LCMS (Method C): RT 1.66 min [M+H]+ 220.1.

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 was 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-e44211fa9b8b46108dafe3f5851b5bce
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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