Hydrochloric Acid → Olamufloxacin

HRID 1078270Notes

Reaction equation

HRID 1078270 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:13]2[CH2:19][C@@H:18]([NH:20]C(=O)C(F)(F)F)[C:15]3([CH2:17][CH2:16]3)[CH2:14]2)[C:9]([CH3:27])=[C:8]2[C:3]=1[C:4](=[O:34])[C:5]([C:31]([OH:33])=[O:32])=[CH:6][N:7]2[CH:28]1[CH2:30][CH2:29]1.[OH-].[K+].Cl>O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:13]2[CH2:19][C@@H:18]([NH2:20])[C:15]3([CH2:16][CH2:17]3)[CH2:14]2)[C:9]([CH3:27])=[C:8]2[C:3]=1[C:4](=[O:34])[C:5]([C:31]([OH:33])=[O:32])=[CH:6][N:7]2[CH:28]1[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 536390245-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methyl-4-oxo-7-((S)-7-trifluoroacetylamino-5-azaspiro[2.4]hept-5-yl)quinoline-3-carboxylic acid

Product 1

HCID 477670OlamufloxacinYield 100.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.26 g of 5-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methyl-4-oxo-7-((S)-7-trifluoroacetylamino-5-azaspiro[2.4]hept-5-yl)quinoline-3-carboxylic acid, 0.18 g of potassium hydroxide and 1.8 ml of water was stirred at room temperature for 0.5 hour. The reaction mixture was neutralized with 10% hydrochloric acid to pH 8, the deposited crystals were collected by filtration and washed with water to give 0.21 g of the desired compound, which was recrystallized from acetonitrile to afford 0.16 g of yellow prisms, m.p. 216.5°-218° C.

Workup

  1. filtrationthe deposited crystals were collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-cb503b30a66b40c581dd48da3172ecb1
Source dataset
uspto-grants-1996_08
Patent number
US05547962

Reaction notes

Loading…