Trifluoroacetic acid → HCID 67953243, compound

HRID 469732Notes

Reaction equation

HRID 469732 reaction equation
C(O[C:6](=O)[N:7]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19](=[O:20])[CH2:18][CH2:17][C@H:16]2[C:21](=[O:32])[NH:22][C:23]2[CH:27]=[C:26]([C:28]([CH3:31])([CH3:30])[CH3:29])[O:25][N:24]=2)=[CH:11][CH:10]=1)C)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:28]([C:26]1[O:25][N:24]=[C:23]([NH:22][C:21]([C@@H:16]2[CH2:17][CH2:18][C:19](=[O:20])[N:15]2[C:12]2[CH:13]=[CH:14][C:9]([NH:7][CH3:6])=[CH:10][CH:11]=2)=[O:32])[CH:27]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67773001HCID 67773001, compound

Product 1

HCID 67953243HCID 67953243, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {4-[(S)-2-(5-tert-butyl-isoxazol-3-ylcarbamoyl)-5-oxo-pyrrolidin-1-yl]-phenyl}-methyl-carbamic acid tert-butyl ester (550 mg, 1.21 mmol) in dichloromethane (5 mL) is cooled in an ice bath. A pre-cooled trifluoroacetic acid (15 mL) is added and the mixture is kept in ice-bath for 30 minutes. Trifluoroacetic acid is evaporated in vacuo, and the residue is treated with ice and sodium bicarbonate solution. Extracted with ethyl acetate (1×150 mL) and the combined extracts washed with brine (50 mL) dried over anhydrous Na2SO4 and solvent removed in vacuo to give the title compound, ESI m/z 357 [M+H]+.

Workup

  1. customfor 30 minutes
  2. customTrifluoroacetic acid is evaporated in vacuo
  3. additionthe residue is treated with ice and sodium bicarbonate solution
  4. extractionExtracted with ethyl acetate (1×150 mL)
  5. washthe combined extracts washed with brine (50 mL)
  6. dry with materialdried over anhydrous Na2SO4 and solvent
  7. customremoved in vacuo

Sources & evidence

ORD record
ord-bc4d82101d3a400185addd002b3c7673
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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