Trifluoroacetic acid → HCID 68158027, compound

HRID 242955Notes

Reaction equation

HRID 242955 reaction equation
C(O[C:6](=O)[N:7]([C@H:9]([C:11]1[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:14]2[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:13]=2[N:12]=1)[CH3:10])C)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:26][C:23]1[CH:24]=[CH:25][C:13]2[N:12]=[C:11]([C@@H:9]([NH:7][CH3:6])[CH3:10])[N:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:14]=2[CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157029HCID 68157029, compound

Product 1

HCID 68158027HCID 68158027, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]methylcarbamic acid tert-butyl ester (0.264 g, 0.72 mmol) in DCM (8 mL) was added TFA (4 mL) and the mixture stirred at RT for 1.5 h. The volatiles were removed under in vacuo and the resulting residue partitioned between DCM and a saturated aqueous solution of NaHCO3. The two phase system was stirred for 10 minutes and then the aqueous phase extracted with DCM. The combined organic fractions were dried (MgSO4) and concentrated in vacuo to afford the title compound as a colourless oil (102 mg, 53%). LCMS (Method J): RT 1.80 min [M+H]+ 270.2.

Workup

  1. customThe volatiles were removed under in vacuo
  2. customthe resulting residue partitioned between DCM
  3. stirringThe two phase system was stirred for 10 minutes
  4. extractionthe aqueous phase extracted with DCM
  5. dry with materialThe combined organic fractions were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a1b12d5bde8f4362aa283dc922d5312d
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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