Trifluoroacetic acid → (R)-1-(1-benzyl-3-(2,5-difluorophenyl)-1H-1,2,4-triazol-5-yl)-2,2-dimethylpropan-1-amine

HRID 1037482Notes

Reaction equation

HRID 1037482 reaction equation
[CH2:1]([N:8]1[C:12]([C@H:13]([NH:18]C(=O)OC(C)(C)C)[C:14]([CH3:17])([CH3:16])[CH3:15])=[N:11][C:10]([C:26]2[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=2[F:33])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([N:8]1[C:12]([C@H:13]([NH2:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[N:11][C:10]([C:26]2[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=2[F:33])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59781123(R)-tert-Butyl 1-(1-benzyl-3-(2,5-difluorophenyl)-1H-1,2,4-triazol-5-yl)-2,2-dimethylpropylcarbamate

Product 1

HCID 59781121(R)-1-(1-benzyl-3-(2,5-difluorophenyl)-1H-1,2,4-triazol-5-yl)-2,2-dimethylpropan-1-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-tert-Butyl 1-(1-benzyl-3-(2,5-difluorophenyl)-1H-1,2,4-triazol-5-yl)-2,2-dimethylpropylcarbamate (3.25 g, 7.13 mmol) was treated with TFA (10 mL) in CH2Cl2 (30 ml). Once the reaction was complete, the reaction was concentrated in vacuo and then partitioned between EtOAc and saturated aqueous NaHCO3 solution. The organics were separated, then washed with H2O, brine, then dried over Na2SO4, filtered, and evaporated under reduced pressure to give (R)-1-(1-benzyl-3-(2,5-difluorophenyl)-1H-1,2,4-triazol-5-yl)-2,2-dimethylpropan-1-amine which was directly used for the next step without further purification (2.32 g, 91%). LC/MS (uplc): MH+ 357.1, 0.82 min.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. custompartitioned between EtOAc and saturated aqueous NaHCO3 solution
  3. customThe organics were separated
  4. washwashed with H2O, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ab88ff3e1d834560bb2aed2967ca1656
Source dataset
uspto-grants-2013_10
Patent number
US08546434B2

Reaction notes

Loading…