Water → Levofloxacin Hydrate

HRID 2244556Notes

Reaction equation

HRID 2244556 reaction equation
FC1C(F)=C2[O:9]C[C@H](C)N3C=C(C(O)=O)C(=O)C(C=1)=C23.CN1CCNCC1.[CH3:28][C@@H:29]1[N:50]2[C:33]3[C:34]([C:46]([C:48]([C:51]([OH:53])=[O:52])=[CH:49]2)=[O:47])=[CH:35][C:36]([F:45])=[C:37]([N:38]2[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]2)[C:32]=3[O:31][CH2:30]1.O>C(O)(C)C>[CH3:28][C@@H:29]1[N:50]2[CH:49]=[C:48]([C:51]([OH:53])=[O:52])[C:46]([C:34]3=[CH:35][C:36]([F:45])=[C:37]([N:38]4[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]4)[C:32](=[C:33]23)[O:31][CH2:30]1)=[O:47].[CH3:28][C@@H:29]1[N:50]2[CH:49]=[C:48]([C:51]([OH:53])=[O:52])[C:46]([C:34]3=[CH:35][C:36]([F:45])=[C:37]([N:38]4[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]4)[C:32](=[C:33]23)[O:31][CH2:30]1)=[O:47].[OH2:9]

Participants

6

Reactant 4

HCID 962Water2×HCID 531671-MethylpiperazineHCID 149096LevofloxacinHCID 688333Levofloxacin q-acid

Product 1

HCID 3033924Levofloxacin Hydrate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Accordingly in the present invention reacting (S)-(-) 9,10-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4] benzoxazine-6-carboxylic acid with N-methyl piperazine yields crude levofloxacin. Suspending crude levofloxacin in isopropanol, addition of known quantity of water to make-up the water content to about 12% to about 20% followed by precipitation affords the levofloxacin hemihydrate.

Workup

  1. customyields crude levofloxacin
  2. customfollowed by precipitation

Sources & evidence

ORD record
ord-f8ece16a490046869f1ab8ccf68b4570
Source dataset
uspto-grants-2010_03
Patent number
US07678903B2

Reaction notes

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