Dimethyl Sulfoxide → Gatifloxacin

HRID 30450

Reaktionsgleichung

Reaktionsgleichung von HRID 30450
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

Komponenten

5

Edukt 3

HCID 679Dimethyl Sulfoxide2×HCID 660572-MethylpiperazineHCID 17956339Gatifloxacin hydrochloride

Produkt 1

HCID 5379Gatifloxacin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
48 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-008428864d23457fbaa80699c21184b4
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423153B2

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