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Cesium carbonate → HCID 68867360、化合物

HRID 1985180
ノート
印刷プレビュー

反応式

HRID 1985180 の反応式
[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[CH3:23][C:24]1[CH:52]=[CH:51][C:27]([CH2:28][N:29]2[CH2:33][CH:32]([CH2:34][CH2:35]OS(C3C=CC(C)=CC=3)(=O)=O)[N:31]([CH2:47][CH2:48][CH3:49])[C:30]2=[O:50])=[CH:26][CH:25]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:35][CH2:34][CH:32]2[CH2:33][N:29]([CH2:28][C:27]3[CH:51]=[CH:52][C:24]([CH3:23])=[CH:25][CH:26]=3)[C:30](=[O:50])[N:31]2[CH2:47][CH2:48][CH3:49])=[CH:9][CH:8]=1)[CH3:2]
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 11220314Ethyl 3-(4-hydroxyphenyl)-2-methyl-2-phenoxypropionateHCID 57719317HCID 57719317、化合物

生成物 1

HCID 68867360HCID 68867360、化合物収率 68.6%

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-methyl-2-phenoxy-propionic acid ethyl ester (0.80 g, 2.66 mmol), toluene-4-sulfonic acid 2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-imidazolidin-4-yl]-ethyl ester (1.26 g, 2.93 mmol) and Cs2CO3 (1.04 g, 3.19 mmol) in DMF (40 mL) is heated to 55° C. under N2 for 17 h. The reaction is cooled and quenched with 1 N HCl (20 mL) and worked up extractively with Et2O and water. The organic layer is dried and the solvent removed to afford crude product that is purified by flash chromatography using 7:1 hexanes:acetone to afford 1.02 g (68%) 2-methyl-3-(4-{2-[1-(4-methyl-benzyl)-2-oxo-3-propyl-imidazolidin-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid ethyl ester. The diasteriomeric products were separated by chiral HPLC (90:10 heptane:IPA, 280 mL/min, 220 nm,) to give products in >99% de. Rf=0.49 (1:1 acetone:hexanes). 1H NMR. MS (ES+) Calc'd for C34H43N2O5 (M+1) 559. Found m/z 559 (100%).

後処理

  1. temperatureThe reaction is cooled
  2. customquenched with 1 N HCl (20 mL)
  3. customThe organic layer is dried
  4. customthe solvent removed
  5. customto afford crude product that
  6. customis purified by flash chromatography

出典と根拠

ORDレコード
ord-4e5d4890e1904f229732685ea40ba951
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