Trifluoroacetic acid → HCID 59410110, compound

HRID 1805185Notes

Reaction equation

HRID 1805185 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=[C:3]1[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:25][CH2:24][CH2:23][C@@H:22]2[C:26]([O:28]C(C)(C)C)=[O:27])=[CH:17][C:16]=1[C:33]([F:36])([F:35])[F:34])=[O:13].C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=[C:3]1[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:25][CH2:24][CH2:23][C@@H:22]2[C:26]([OH:28])=[O:27])=[CH:17][C:16]=1[C:33]([F:36])([F:35])[F:34])=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59410039HCID 59410039, compound

Product 1

HCID 59410110HCID 59410110, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (2R)-1-[4-[(4-oxo1H-quinoline-3-carbonyl)amino]-3-(trifluoromethyl)phenyl]pyrrolidine-2-carboxylate (35 mg, 0.06979 mmol) in DCM (500 μL) was added TFA (1 mL) at room temperature and the reaction mixture was stirred for 3 h. The solvents were evaporated under reduced pressure and the residue was purified via reverse phase HPLC to give (2R)-1-[4-[(4-oxo-1H-quinoline-3-carbonyl)amino]-3-(trifluoromethyl)phenyl]pyrrolidine-2-carboxylic acid. LC/MS: m/z 466.3 (M+H)+ at 1.46 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. customthe residue was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-a93cb951b6ae45bd9138ced933ba8a05
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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