Potassium Iodide → 1-Cyclopropyl-7-[4-(diethoxyphosphinyl)-1-piperazinyl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid, 2-Methoxyethyl Ester

HRID 1461720

Reaktionsgleichung

Reaktionsgleichung von HRID 1461720
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:28])=[C:11]([N:14]4[CH2:19][CH2:18][N:17]([P:20]([O:25][CH2:26][CH3:27])([O:22][CH2:23][CH3:24])=[O:21])[CH2:16][CH2:15]4)[CH:12]=3)[C:7](=[O:29])[C:6]([C:30]([OH:32])=[O:31])=[CH:5]2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:39][O:40][CH2:41][CH2:42]Br.[OH-].[K+].[I-].[K+]>CN(C)P(N(C)C)(N(C)C)=O.CCOCC>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:28])=[C:11]([N:14]4[CH2:19][CH2:18][N:17]([P:20]([O:22][CH2:23][CH3:24])([O:25][CH2:26][CH3:27])=[O:21])[CH2:16][CH2:15]4)[CH:12]=3)[C:7](=[O:29])[C:6]([C:30]([O:32][CH2:42][CH2:41][O:40][CH3:39])=[O:31])=[CH:5]2)[CH2:3][CH2:2]1

Komponenten

8

Edukt 5

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 14797Potassium HydroxideHCID 809722-Bromoethyl methyl etherHCID 150280071-Cyclopropyl-7-[4-(diethoxyphosphinyl)-1-piperazinyl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid

Produkt 1

HCID 150280151-Cyclopropyl-7-[4-(diethoxyphosphinyl)-1-piperazinyl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid, 2-Methoxyethyl EsterAusbeute 80,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 12679HexamethylphosphoramideLösungsmittel

Versuchsvorschrift

To a solution of 0.467 g of the product of Example 40 in 5 ml of hexamethylphosphoramide was added 0.163 g of cesium carbonate, 0.304 g of 2-bromoethyl methyl ether, 0.137 g of 45% aqueous potassium hydroxide and 0.017 g of potassium iodide. The suspension was stirred in the dark under argon for 8 days. Ether (40 ml) was added and the mixture was extracted successively with water, brine and water. The ether layer was discarded. The aqueous layers were extracted with chloroform, the chloroform extracts were dried over sodium sulfate and then evaporated, finally at <100° and 0.06 mm. to remove hexamethylphosphoramide. Two recrystallizations of the solid residue from methylene chloride-n-heptane gave 0.424 g of ivory-colored needles, m.p. 138°-141° C. The product was easily soluble in water and in 0.1M phosphate buffer, pH 7.5.

Aufarbeitung

  1. extractionthe mixture was extracted successively with water, brine and water
  2. extractionThe aqueous layers were extracted with chloroform
  3. dry with materialthe chloroform extracts were dried over sodium sulfate
  4. customevaporated, finally at <100°
  5. customto remove hexamethylphosphoramide
  6. customTwo recrystallizations of the solid residue from methylene chloride-n-heptane

Quellen und Nachweise

ORD-Eintrag
ord-efff3b121e6640bda6417591961f62c2
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05077283

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