Hydrochloric Acid → Pazufloxacin

HRID 981294Notes

Reaction equation

HRID 981294 reaction equation
Cl.[NH2:2][C:3]1([C:6]2[C:7]([F:24])=[CH:8][C:9]3[C:19](=[O:20])[C:18]([C:21]([OH:23])=[O:22])=[CH:17][N:11]4[C@@H:12]([CH3:16])[CH2:13][O:14][C:15]=2[C:10]=34)[CH2:5][CH2:4]1.[OH-].[K+].C(O)C.Cl>O>[NH2:2][C:3]1([C:6]2[C:7]([F:24])=[CH:8][C:9]3[C:19](=[O:20])[C:18]([C:21]([OH:23])=[O:22])=[CH:17][N:11]4[C@@H:12]([CH3:16])[CH2:13][O:14][C:15]=2[C:10]=34)[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 45108234Pazufloxacin hydrochloride

Product 1

HCID 65957PazufloxacinYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

In 8.57 ml of water was dissolved 730 mg of (S)-10-(1-aminocyclopropyl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid hydrochloride, and to the resulting solution were added 242 mg of potassium hydroxide and 5.84 ml of ethanol in this order. Subsequently, 0.19 ml of conc. hydrochloric acid was dropped thereinto at 60° C. in 30 minutes, and thereafter, the resulting mixture was cooled to 20° C. in 2 hours. The mixture was stirred at 20° C. for a further 30 minutes, and the resulting crystals were collected by filtration to obtain 570 mg (yield: 87.0%) of (S)-10-(1-aminocyclopropyl)-9-fluoro-3-methyl-7-oxo2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid.

Workup

  1. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-1d555086efcc47e192436542243dfe73
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

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