Dichloromethane → Pazufloxacin

HRID 981287Notes

Reaction equation

HRID 981287 reaction equation
C(OC([NH:11][C:12]1([C:15]2[C:16]([F:35])=[CH:17][C:18]3[C:28](=[O:29])[C:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:26][N:20]4[C@@H:21]([CH3:25])[CH2:22][O:23][C:24]=2[C:19]=34)[CH2:14][CH2:13]1)=O)C1C=CC=CC=1.[H][H].C(Cl)Cl.C(=O)([O-])O.[Na+]>C(O)(=O)C.[C].[Pd].O>[NH2:11][C:12]1([C:15]2[C:16]([F:35])=[CH:17][C:18]3[C:28](=[O:29])[C:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:26][N:20]4[C@@H:21]([CH3:25])[CH2:22][O:23][C:24]=2[C:19]=34)[CH2:13][CH2:14]1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 9982606HCID 9982606, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54380043PazufloxacinYield 89.2%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In 100 ml of acetic acid was dissolved 10 g of ethyl (S)-10-(1-benzyloxycarbonylaminocyclopropyl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate. To the resulting solution was added 2 g of 5% palladium-carbon. The resulting mixture was stirred at room temperature for 2 hours at atmospheric pressure in a hydrogen stream. The reaction mixture was filtered. The filtrate was concentrated to dryness under reduced pressure. To the residue obtained were added 200 ml of methylene chloride and 200 ml of water in this order. The resulting mixture was adjusted to pH 7.7 with a saturated aqueous sodium hydrogen-carbonate 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. Diethyl ether was added to the residue obtained. The resulting crystals were collected by filtration to obtain 6.43 g (yield: 89.2%) of ethyl (S)-10-(1-aminocyclopropyl)-9-fluoro-3-methyl- 7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated to dryness 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
  8. additionDiethyl ether was added to the residue
  9. customobtained
  10. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-79210a3ea4bc47ad8da84bf14daf6c82
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

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