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Cesium carbonate → Methyl 4-{[3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}benzoate

HRID 536543
ノート
印刷プレビュー

反応式

HRID 536543 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:14][CH:15]([OH:20])[C:16]([F:19])([F:18])[F:17])[C:10](=[O:13])[NH:11][N:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:28][C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=1>CC(C)=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:14][CH:15]([OH:20])[C:16]([F:18])([F:19])[F:17])[C:10](=[O:13])[N:11]([CH2:28][C:29]3[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=3)[N:12]=2)=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 584601185-(4-Chlorophenyl)-4-(3,3,3-trifluoro-2-hydroxypropyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

生成物 1

HCID 58460117Methyl 4-{[3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}benzoate

試薬・触媒・溶媒 2

HCID 180
Acetone
溶媒
HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

An amount of 305 mg (0.99 mmol) of the compound from Example 19A and 355 mg (1.09 mmol) of caesium carbonate were suspended in 10 ml of acetone and admixed with 227 mg (0.99 mmol) of methyl 4-(bromomethyl)benzoate. The mixture was stirred at 50° C. for 3 h. The suspension was diluted with water. It was extracted with twice 15 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate and freed from the solvent on a rotary evaporator. Purification by flash chromatography over silica gel with elution with cyclohexane/ethyl acetate (gradient 10:1→2:1) gave 284 mg (63% of theory) of the target compound.

後処理

  1. extractionIt was extracted with twice 15 ml of ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulphate
  3. customfreed from the solvent on a rotary evaporator
  4. customPurification by flash chromatography over silica gel
  5. washwith elution with cyclohexane/ethyl acetate (gradient 10:1→2:1)
  6. customgave 284 mg (63% of theory) of the target compound

出典と根拠

ORDレコード
ord-0664335491bd4ea48bfc07c6ca04e7d7
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08859601B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート