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Cesium carbonate → 2-Cyclopentyloxy-3-(4-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid cyclopentyl ester

HRID 1985257
ノート
印刷プレビュー

反応式

HRID 1985257 の反応式
[CH:1]1([O:6][C:7](=[O:23])[CH:8]([O:17][CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:24][N:25]1[CH:29]([CH2:30][CH2:31]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:28][N:27]([CH2:43][C:44]2[CH:49]=[CH:48][C:47]([C:50]([F:53])([F:52])[F:51])=[CH:46][CH:45]=2)[C:26]1=[O:54].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH:1]1([O:6][C:7](=[O:23])[CH:8]([O:17][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)[CH2:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:31][CH2:30][CH:29]3[CH2:28][N:27]([CH2:43][C:44]4[CH:49]=[CH:48][C:47]([C:50]([F:52])([F:53])[F:51])=[CH:46][CH:45]=4)[C:26](=[O:54])[N:25]3[CH3:24])=[CH:14][CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5]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

5

反応物 3

HCID 10796Cesium carbonateHCID 68869672HCID 68869672、化合物HCID 86596229HCID 86596229、化合物

生成物 1

HCID 688693802-Cyclopentyloxy-3-(4-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid cyclopentyl ester収率 64%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒

反応条件

温度
65 °C

実験手順

A mixture of 2-cyclopentyloxy-3-(4-hydroxy-phenyl)-propionic acid cyclopentyl ester(0.090 g, 0.283 mmol), toluene-4-sulfonic acid 2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethyl ester (0.140 g, 0.307 mmol) and Cs2CO3 (0.138 g, 0.423 mmol) in DMF (10 mL) was heated to 65° C. under N2 for 16 h. The reaction was cooled and quenched with 1 N HCl (10 mL) and worked up extractively with Et2O and water. The organic layer was dried (MgSO4) and the solvent removed in vacuo to afford crude product that was purified by flash chromatography using 3:1 hexanes:acetone to afford 0.108 g (64%) 2-cyclopentyloxy-3-(4-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid cyclopentyl ester. 1H NMR. MS (ES+) Calc'd for C33H42N2O5F3 (M+1) 603. Found m/z 603 (100%).

後処理

  1. temperatureThe reaction was cooled
  2. customquenched with 1 N HCl (10 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customto afford crude product that
  6. customwas purified by flash chromatography

出典と根拠

ORDレコード
ord-1ba98cce38f944299e52dd808953e5e4
出典データセット
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07544812B2

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