Dimethyl Sulfoxide → Gatifloxacin

HRID 30450

Reaction equation

CS(C)=O.CC1CNCCN1.[CH3:12][CH:13]1[NH:18][CH2:17][CH2:16][N:15]([C:19]2[C:24]([O:25][CH3:26])=[C:23]3[N:27]([CH:35]4[CH2:37][CH2:36]4)[CH:28]=[C:29]([C:32]([OH:34])=[O:33])[C:30](=[O:31])[C:22]3=[CH:21][C:20]=2[F:38])[CH2:14]1.Cl>O>[CH3:12][CH:13]1[NH:18][CH2:17][CH2:16][N:15]([C:19]2[C:24]([O:25][CH3:26])=[C:23]3[N:27]([CH:35]4[CH2:37][CH2:36]4)[CH:28]=[C:29]([C:32]([OH:34])=[O:33])[C:30](=[O:31])[C:22]3=[CH:21][C:20]=2[F:38])[CH2:14]1

Participants

Conditions

Temperature: 48 °C

Procedure

A 140 liter reactor equipped with mechanical stirrer, condenser and thermometer, was charged with dimethyl sulfoxide (DMSO, 120 L). The DMSO was heated to 55° C. and the reactor was charged with 2-methylpiperazine (8.6 kg). Gatifloxacin acid was charged, in four portions, every 2 hours (3×4=12 Kg). The reaction mixture was stirred at a rate of 110 rpm under nitrogen atmosphere. The temperature was maintained for 24 hours until completion of the reaction. The reaction mixture was cooled to 48° C. and water (24 L) was added at this temperature. The mixture was cooled to 5° C. during 3.5 hours and maintained with stirring for 15 hours at this temperature. The mixture was filtered (suction) and washed with acetonitrile (18 L) to obtain 15.9 Kg of gatifloxacin.

Workup

customA 140 liter reactor equipped with mechanical stirrer, condenser
temperatureThe temperature was maintained for 24 hours until completion of the reaction
temperatureThe mixture was cooled to 5° C. during 3.5 hours
temperaturemaintained
stirringwith stirring for 15 hours at this temperature
filtrationThe mixture was filtered (suction)
washwashed with acetonitrile (18 L)

Sources & evidence

ORD record: ord-008428864d23457fbaa80699c21184b4
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423153B2

Linked notes

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