Levofloxacin → Levofloxacin Hydrate

HRID 31374

Reaction equation

[CH3:1][C@@H:2]1[N:23]2[C:6]3[C:7]([C:19]([C:21]([C:24]([OH:26])=[O:25])=[CH:22]2)=[O:20])=[CH:8][C:9]([F:18])=[C:10]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[C:5]=3[O:4][CH2:3]1>C(#N)C.O>[CH3:1][C@@H:2]1[N:23]2[CH:22]=[C:21]([C:24]([OH:26])=[O:25])[C:19]([C:7]3=[CH:8][C:9]([F:18])=[C:10]([N:11]4[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]4)[C:5](=[C:6]23)[O:4][CH2:3]1)=[O:20].[CH3:1][C@@H:2]1[N:23]2[CH:22]=[C:21]([C:24]([OH:26])=[O:25])[C:19]([C:7]3=[CH:8][C:9]([F:18])=[C:10]([N:11]4[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]4)[C:5](=[C:6]23)[O:4][CH2:3]1)=[O:20].[OH2:4]

Participants

Conditions

Temperature: 0 °C

Procedure

25 g of wet levofloxacin crude (about 22.17 g or dry levofloxacin) was put in suspension in 225 mL of mixture ACN:H2O (99:1) under nitrogen atmosphere. The mixture was heated to reflux during 1 hour and then filtrated under vacuum with Hyflow when still hot. Then the solution was heated again to reflux and cooled to 0° C. over a period of 1 hour. The precipitate was filtrated under vacuum, washed with ACN:H2O (2×12 mL) and dried in a vacuum oven to give 18.6 g (84%) of purified levofloxacin hemihydrate. The purified levofloxacin hemihydrate contained approximately one-third less desmethyl levofloxacin than in the crude sample.

Workup

temperatureThe mixture was heated
temperatureto reflux during 1 hour
filtrationfiltrated under vacuum with Hyflow when still hot
temperatureThen the solution was heated again
temperatureto reflux
filtrationThe precipitate was filtrated under vacuum
washwashed with ACN
dry with materialH2O (2×12 mL) and dried in a vacuum oven

Sources & evidence

ORD record: ord-3a561d923a7b4eb78c307814fe5df863
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425628B2

Linked notes

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