Isopropanol → 4-(1-(2-Fluoro-4-biphenylyl)ethyl)-2-methylamino-5-thiazolecarboxylic acid

HRID 256771

反応式

HRID 256771 の反応式
[CH:1]([C:3]1[S:7][C:6]([NH:8][CH3:9])=[N:5][C:4]=1[CH:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:14]([F:24])[CH:13]=1)[CH3:11])=[O:2].CC(C)=[O:27].OS(O)(=O)=O.O=[Cr](=O)=O.[Cr](O)(O)(=O)=O.CC(O)C>CC(C)=O.S(=O)(=O)(O)O.O>[F:24][C:14]1[CH:13]=[C:12]([CH:10]([C:4]2[N:5]=[C:6]([NH:8][CH3:9])[S:7][C:3]=2[C:1]([OH:27])=[O:2])[CH3:11])[CH:17]=[CH:16][C:15]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

8

反応物 4

HCID 3776IsopropanolHCID 24425Chromic AcidHCID 197855435-Formyl-4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-methylaminothiazoleHCID 131709961Jones' reagent2 回

生成物 1

HCID 197855604-(1-(2-Fluoro-4-biphenylyl)ethyl)-2-methylamino-5-thiazolecarboxylic acid収率 20%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 1118Sulfuric Acid溶媒

実験手順

5-Formyl-4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-methylaminothiazole (1.00 g, 2.9 mmoles) was dissolved in acetone (20 ml). Jones reagent (chromic acid (VI) dissolved in a mixture of concentrated sulfuric acid and water) (2 ml) was added dropwise thereinto while cooling the system with ice, after which it was stirred for one hour. Then, an additional 2 ml of Jones reagent was added dropwise and the resulting mixture was stirred for one hour. A small quantity of 2-propyl alcohol was added to the reaction mixture, it was extracted with ether, and the ether layer was washed with water and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was recrystallized from ethyl acetate to obtain the desired 4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-methylamino-5-thiazolecarboxylic acid (205 mg, 0.58 mmole, yield 20%) as a white crystalline product.

後処理

  1. additionwas added dropwise
  2. temperaturewhile cooling the system with ice
  3. stirringthe resulting mixture was stirred for one hour
  4. extractionwas extracted with ether
  5. washthe ether layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-9a21952cd5604db0878d4fd1b474390a
出典データセット
uspto-grants-1993_11
特許番号
US05258396

関連ノート

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