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

HRID 2253274노트

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HRID 2253274 반응식
[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

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 69684CyclohexylureaHCID 69131096HCID 69131096, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 2723922Sodium ethoxide용매

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온도
75 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-5b6832600898468d80bc84d955293681
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07323496B2

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