Acetonitrile → Gatifloxacin

HRID 1594377Notes

Reaction equation

HRID 1594377 reaction equation
C(#N)C.[OH-].[Na+].[CH3:6][CH:7]1[NH:12][CH2:11][CH2:10][N:9]([C:13]2[C:18]([O:19][CH3:20])=[C:17]3[N:21]([CH:29]4[CH2:31][CH2:30]4)[CH:22]=[C:23]([C:26]([OH:28])=[O:27])[C:24](=[O:25])[C:16]3=[CH:15][C:14]=2[F:32])[CH2:8]1.Cl>O>[CH3:6][CH:7]1[NH:12][CH2:11][CH2:10][N:9]([C:13]2[C:18]([O:19][CH3:20])=[C:17]3[N:21]([CH:29]4[CH2:31][CH2:30]4)[CH:22]=[C:23]([C:26]([OH:28])=[O:27])[C:24](=[O:25])[C:16]3=[CH:15][C:14]=2[F:32])[CH2:8]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 17956339Gatifloxacin hydrochloride

Product 1

HCID 5379Gatifloxacin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a further aspect, the present invention relates to a method of making a crystalline form of gatifloxacin having at least one characteristic of form Y including the steps of: providing a slurry of gatifloxacin hydrochloride in a 9:1, vol:vol, mixture of acetonitrile and water at a temperature of about 5° C., combining the suspension with a volume of an aqueous solution of NaOH sufficient to neutralize at least about 70 mole % of the hydrochloride, isolating solid gatifloxacin from the resulting suspension, washing the isolated solid gatifloxacin with a 9:1, v:v mixture of acetonitrile and water, and drying the isolated solid gatifloxacin at about 50° C. and reduced pressure to obtain the crystalline form of gatifloxacin having at least one characteristic of form Y.

Sources & evidence

ORD record
ord-0e899ce7513f4019b0512119423a3a05
Source dataset
uspto-grants-2007_11
Patent number
US07301024B2

Reaction notes

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