Trifluoroacetic acid → HCID 67496508, compound

HRID 1628347Notes

Reaction equation

HRID 1628347 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:13]=[C:12]([NH:14][C:15](=[O:32])[C@@H:16]([NH:24]C(=O)OC(C)(C)C)[CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:11]([CH3:33])[N:10]=2)[CH:6]=[CH:5][N:4]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:24][C@@H:16]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:15]([NH:14][C:12]1[N:11]([CH3:33])[N:10]=[C:9]([C:7]2[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[CH:8]=2)[CH:13]=1)=[O:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70865490HCID 70865490, compound

Product 1

HCID 67496508HCID 67496508, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 50 ml flask was added tert-butyl (S)-1-(3-(2-methoxypyridin-4-yl)-1-methyl-1H-pyrazol-5-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamate 105.1.D (0.99 g, 2.19 mmole) and 20 ml of dichloromethane. To the solution, 5 ml of trifluoroacetic acid was added. The reaction was stirred at room temperature for 2.5 hours at which time the solvent was removed by rotary evaporation. The residue was suspended in ethyl acetate, and washed successively with saturated sodium bicarbonate, water and brine. The organic layer was dried over anhydrous sodium sulfate, and concentrated in vacuo to give 105.1.E (706 mg, 92% yield) as yellow solid.

Workup

  1. customwas removed by rotary evaporation
  2. washwashed successively with saturated sodium bicarbonate, water and brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bdd395282fc64333b7047f3323e3fdf2
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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