Trifluoroacetic acid → HCID 57950512, compound

HRID 598884Notes

Reaction equation

HRID 598884 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]3[N:15]=[C:14]([CH2:16][CH2:17][C@@H:18]([NH:30]C(=O)OC(C)(C)C)[CH2:19][C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)[O:13][N:12]=3)[CH:8]=2)[NH:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:30][C@@H:18]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:24][CH:25]=1)[CH2:17][CH2:16][C:14]1[O:13][N:12]=[C:11]([C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[NH:3][C:2](=[O:1])[CH2:10]3)[N:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68373023HCID 68373023, compound

Product 1

HCID 57950512HCID 57950512, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl(R)-4-(3-(2-oxoindolin-5-yl)-1,2,4-oxadiazol-5-yl)-1-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate (200 mg, 0.37 mmol) was dissolved in 5.0 mL anhydrous DCM, and 5.0 mL TFA was added. After 30 minutes stirring at room temperature, the solvent was evaporated and the residue was taken up in 100 mL EtOAc. To the resulting solution was added 50 mL of saturated aqueous sodium bicarbonate and 30 mL 5% aqueous sodium carbonate. The organic layer was washed with brine and dried over sodium sulfate to afford the product as a white solid (130 mg, 81%). MS (API-ES) m/z (%): 417.1 (100%, M++H).

Workup

  1. customthe solvent was evaporated
  2. additionTo the resulting solution was added 50 mL of saturated aqueous sodium bicarbonate and 30 mL 5% aqueous sodium carbonate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-7f5b23324c324fcab63e3b488a6abe5e
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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