Trifluoroacetic acid → HCID 68157212, compound

HRID 242903Notes

Reaction equation

HRID 242903 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:13]2[CH:21]=[CH:22][C:23]([F:25])=[CH:24][C:12]=2[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:25][C:23]1[CH:22]=[CH:21][C:13]2[N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:10]([C@@H:8]([NH2:7])[CH3:9])=[N:11][C:12]=2[CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58459222HCID 58459222, compound

Product 1

HCID 68157212HCID 68157212, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-(5-fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester (661 mg, 1.9 mmol) in DCM (9 mL) was added TFA (4.5 mL) and the mixture stirred at RT for 2 h. The volatiles were removed in vacuo and the resulting residue partitioned between DCM (20 mL) and a saturated aqueous solution of NaHCO3 (40 mL). The two phase system was stirred for 10 min, then the organic fraction 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 (379 mg, 78%). LCMS (Method J): RT 1.77 min [M+H]+ 256.2.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe resulting residue partitioned between DCM (20 mL)
  3. stirringThe two phase system was stirred for 10 min
  4. dry with materialthe organic fraction 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-316bcdf784984d18944d26978e3ae690
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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