Hydrochloric Acid → 2-(4-{4-[3-(3-Cyclohexylureido)-3-Oxopropyl]-Phenoxy}-Phenyl)-3-(3,5-Dimethoxyphenyl)-Acrylic Acid

HRID 2253274ノート

反応式

HRID 2253274 の反応式
[CH:1]1([NH:7][C:8]([NH2:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:21]=[C:22]([C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]3[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][C:41](OCC)=[O:42])=[CH:35][CH:34]=3)=[CH:28][CH:27]=2)[C:23]([OH:25])=[O:24])[CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1.C(O)(C(F)(F)F)=O.Cl>[O-]CC.[Na+].C(O)C>[CH:1]1([NH:7][C:8](=[O:9])[NH:10][C:41](=[O:42])[CH2:40][CH2:39][C:36]2[CH:35]=[CH:34][C:33]([O:32][C:29]3[CH:28]=[CH:27][C:26]([C:22](=[CH:21][C:15]4[CH:16]=[C:17]([O:19][CH3:20])[CH:18]=[C:13]([O:12][CH3:11])[CH:14]=4)[C:23]([OH:25])=[O:24])=[CH:31][CH:30]=3)=[CH:38][CH:37]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 69684CyclohexylureaHCID 69131096HCID 69131096、化合物

生成物 1

HCID 691302652-(4-{4-[3-(3-Cyclohexylureido)-3-Oxopropyl]-Phenoxy}-Phenyl)-3-(3,5-Dimethoxyphenyl)-Acrylic Acid

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 2723922Sodium ethoxide溶媒

反応条件

温度
75 °C

実験手順

Cyclohexylurea (1.3 g, 9 mmol) was dissolved in sodium ethoxide in ethanol (21% w/w, 3 mL) at 75° C. To this solution 5 was added (0.5 g, 1.1 mmol) in one lot. The resulting mixture was stirred at 75° C. for 5 min, then cooled quickly to 40-50° C. TFA (0.5 mL) was added and then 5% aqueous HCl (1N, 0.6 mL). After stirring at room temperature for 1 hr, the mixture was left overnight at 4° C. The solid separated was filtered and refluxed in ethyl acetate (4 mL) for 20 min. The mixture was allowed to cool to room temperature, filtered and the crude product was purified by silica gel chromatography using hexane-ethyl acetate (1:1). Yield: 0.27 g, 45%.

後処理

  1. temperaturecooled quickly to 40-50° C
  2. stirringAfter stirring at room temperature for 1 hr
  3. waitthe mixture was left overnight at 4° C
  4. customThe solid separated
  5. filtrationwas filtered
  6. temperaturerefluxed in ethyl acetate (4 mL) for 20 min
  7. temperatureto cool to room temperature
  8. filtrationfiltered
  9. customthe crude product was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-5b6832600898468d80bc84d955293681
出典データセット
uspto-grants-2008_01
特許番号
US07323496B2

反応ノート

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