Sodium Hydroxide → Gatifloxacin

HRID 1594378Notes

Reaction equation

[OH-].[Na+].[CH3:3][CH:4]1[NH:9][CH2:8][CH2:7][N:6]([C:10]2[C:15]([O:16][CH3:17])=[C:14]3[N:18]([CH:26]4[CH2:28][CH2:27]4)[CH:19]=[C:20]([C:23]([OH:25])=[O:24])[C:21](=[O:22])[C:13]3=[CH:12][C:11]=2[F:29])[CH2:5]1.Cl>>[CH3:3][CH:4]1[NH:9][CH2:8][CH2:7][N:6]([C:10]2[C:15]([O:16][CH3:17])=[C:14]3[N:18]([CH:26]4[CH2:28][CH2:27]4)[CH:19]=[C:20]([C:23]([OH:25])=[O:24])[C:21](=[O:22])[C:13]3=[CH:12][C:11]=2[F:29])[CH2:5]1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 17956339Gatifloxacin hydrochloride

Product 1

HCID 5379Gatifloxacin

Procedure

Gatifloxacin form Y can be made by providing a slurry of gatifloxacin-HCl in acetonitrile:water (90:10, v:v, ca. 16.7% w/v) at about 5° C.; combining the suspension with a volume of aqueous NaOH (e.g. 47%) sufficient to neutralize at least about 70 mole % of the hydrochloride (i.e. convert it to the free base); and isolating solid gatifloxacin from the resulting suspension. The isolated (recovered) gatifloxacin is washed with acetonitrile:water (90:10) and dried at a temperature of about 50° C. at reduced pressure.

Sources & evidence

ORD record: ord-8398e7420ec84e8fa393cc299b4d3274
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07301024B2

Reaction notes

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