Cesium carbonate → HCID 68869796、化合物

HRID 1985253ノート

反応式

HRID 1985253 の反応式
[CH2:1]([O:3][C:4](=[O:16])[CH:5]([O:14][CH3:15])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[CH3:17][N:18]1[CH:22]([CH2:23][CH2:24]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:21][N:20]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=2)[C:19]1=[O:47].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:16])[CH:5]([O:14][CH3:15])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:24][CH2:23][CH:22]2[CH2:21][N:20]([CH2:36][C:37]3[CH:42]=[CH:41][C:40]([C:43]([F:45])([F:46])[F:44])=[CH:39][CH:38]=3)[C:19](=[O:47])[N:18]2[CH3:17])=[CH:11][CH:12]=1)[CH3:2]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 18794793Ethyl 3-(4-hydroxyphenyl)-2-methoxypropanoateHCID 86596229HCID 86596229、化合物

生成物 1

HCID 68869796HCID 68869796、化合物収率 65.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
55 °C

実験手順

A mixture of 3-(4-hydroxy-phenyl)-2-methoxy-propionic acid ethyl ester 0.027 g, 0.120 mmol), toluene-4-sulfonic acid 2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethyl ester (0.061 g, 0.133 mmol) and Cs2CO3 (0.059 g, 0.181 mmol) in DMF (4 mL) was heated to 55° 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 4:1 then 3:1 hexanes:acetone to afford 0.040 g (64%) 2-methoxy-3-(4-{2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-propionic acid ethyl ester. 1H NMR. MS (ES+) Calc'd for C26H32N2O5F3 (M+1) 509. Found m/z 509 (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-ef55995f30034dd3b77b9284716ef2ce
出典データセット
uspto-grants-2009_06
特許番号
US07544812B2

反応ノート

読み込み中…