Trifluoroacetic acid → (1R,2R)-2-Benzyloxy-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)propylamine

HRID 242921Notes

Reaction equation

HRID 242921 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:19]1[N:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:22]2[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:21]=2[N:20]=1)[C@H:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:12]([O:11][C@H:9]([CH3:10])[C@H:8]([NH2:7])[C:19]1[N:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:22]2[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:21]=2[N:20]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157228[(1R,2R)-2-benzyloxy-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)propyl]carbamic acid tert-butyl ester

Product 1

HCID 68157829(1R,2R)-2-Benzyloxy-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)propylamineYield 13.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(1R,2R)-2-benzyloxy-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)propyl]carbamic acid tert-butyl ester (0.971 g, 2.0 mmol) in DCM (15 mL) was added TFA (8 mL) and the mixture stirred at RT for 2 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, 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 (100 mg, 13%). LCMS (Method C): RT 2.59 min [M+H]+ 376.4.

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 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-54f0988959e748699ab3b90388d00b0a
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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