Trifluoroacetic acid → HCID 9825135, compound

HRID 1019050Notes

Reaction equation

HRID 1019050 reaction equation
[N:1]1([CH2:6]/[CH:7]=[CH:8]/[C:9]2[CH:29]=[CH:28][C:12]([C:13]([NH:15][C@@H:16]([CH2:24][CH2:25][S:26][CH3:27])[C:17]([O:19]C(C)(C)C)=[O:18])=[O:14])=[C:11]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[CH:10]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.C(O)(C(F)(F)F)=O>ClCCl>[N:1]1([CH2:6]/[CH:7]=[CH:8]/[C:9]2[CH:29]=[CH:28][C:12]([C:13]([NH:15][C@@H:16]([CH2:24][CH2:25][S:26][CH3:27])[C:17]([OH:19])=[O:18])=[O:14])=[C:11]([C:30]3[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=3)[CH:10]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 9849199HCID 9849199, compound

Product 1

HCID 9825135HCID 9825135, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (2S)-2-{4-[(E)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzamido}-4-methylsulfanylbutyrate (0.2 g; 0.4 mmol) in dichloromethane (2 ml) was treated at 0° C. with TFA (2 ml). The mixture was allowed to warm to ambient temperature and stirred for 1 hour. After evaporation of the solvent, the residue was taken up with distilled water (5 ml); the pH was adjusted to 6 with NH4OH and the solution was purified on reverse phase silica eluting with methanol/ammonium carbonate buffer (2 g/l; pH 7) (40/60) to give the title compound after freeze-drying. Yield: 40%

Workup

  1. customAfter evaporation of the solvent
  2. customthe solution was purified on reverse phase silica eluting with methanol/ammonium carbonate buffer (2 g/l; pH 7) (40/60)

Sources & evidence

ORD record
ord-162ec9c86bfc4beda894c596d1b3e543
Source dataset
uspto-grants-2002_11
Patent number
US06486156B1

Reaction notes

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