Trifluoroacetic acid → HCID 54166271, compound

HRID 981278Notes

Reaction equation

HRID 981278 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:15][C:16]([NH:18][C:19]1([C:22]2[C:31]([F:32])=[C:30]3[C:25]([C:26](=[O:50])[C:27]([C:45]([O:47][CH2:48][CH3:49])=[O:46])=[CH:28][N:29]3[C@@H:33]([CH3:44])[CH2:34][N:35](C(OC(C)(C)C)=O)[CH3:36])=[CH:24][C:23]=2[F:51])[CH2:21][CH2:20]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>O>[CH2:8]([O:15][C:16]([NH:18][C:19]1([C:22]2[C:31]([F:32])=[C:30]3[C:25]([C:26](=[O:50])[C:27]([C:45]([O:47][CH2:48][CH3:49])=[O:46])=[CH:28][N:29]3[C@@H:33]([CH3:44])[CH2:34][NH:35][CH3:36])=[CH:24][C:23]=2[F:51])[CH2:21][CH2:20]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 86744591HCID 86744591, compound

Product 1

HCID 54166271HCID 54166271, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2 ml of trifluoroacetic acid was added, with ice-cooling, 300 mg of ethyl (S)-7-(1-benzyloxycarbonylaminocyclopropyl)-6,8-difluoro-1-[2-(N-tert-butoxycarbonyl-N-methylamino)-1-methylethyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylate. The resulting mixture was stirred at the same temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure. To the residue obtained were added 20 ml of ethyl acetate and 10 ml of water in this order. The resulting mixture was adjusted to pH 8 with a saturated aqueous sodium hydrogencarbonate solution. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 240 mg (yield: 96.0%) of ethyl (S)-7-(1-benzyloxycarbonylaminocyclopropyl)-6,8-difluoro-1-[2-(N-methylamino)-1methylethyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylate.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customTo the residue obtained
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-c3c2c4787aeb4390b36c5168fc2a7bf2
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

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