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

HRID 1460153

反応式

HRID 1460153 の反応式
[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

参加物

8

反応物 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

生成物 1

HCID 150280151-Cyclopropyl-7-[4-(diethoxyphosphinyl)-1-piperazinyl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid, 2-Methoxyethyl Ester収率 80.8%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 12679Hexamethylphosphoramide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4f8af9bdd2ab4625b426bf40a64e63e2
出典データセット
uspto-grants-1991_12
特許番号
US05070082

関連ノート

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