Acetic Acid → 3-[2-Butyl-4-chloro-1-(4-aminobenzyl)imidazol-5-yl] propenoic acid ethyl ester

HRID 653930노트

반응식

HRID 653930 반응식
[CH2:1]([O:3][C:4](=[O:27])[CH:5]=[CH:6][C:7]1[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)[C:10]([CH2:22][CH2:23][CH2:24][CH3:25])=[N:9][C:8]=1[Cl:26])[CH3:2].C(O)(=O)C>C(O)C.[Fe]>[CH2:1]([O:3][C:4](=[O:27])[CH:5]=[CH:6][C:7]1[N:11]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=2)[C:10]([CH2:22][CH2:23][CH2:24][CH3:25])=[N:9][C:8]=1[Cl:26])[CH3:2]

참가 물질

5

반응물 2

HCID 176Acetic AcidHCID 536609323-[2-Butyl-4-chloro-1-(4-nitrobenzyl)imidazol-5-yl]propenoic acid ethyl ester

생성물 1

HCID 543706923-[2-Butyl-4-chloro-1-(4-aminobenzyl)imidazol-5-yl] propenoic acid ethyl ester

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

실험 절차

A mixture of 0.5 g of 3-[2-butyl-4-chloro-1-(4-nitrobenzyl)imidazol-5-yl]-propenoic acid ethyl ester (E isomer) prepared from Part B of Example 227, 1 g of iron and 2 mL of glacial acetic acid in 30 mL of absolute ethanol was refluxed for 1 hour. The reaction mixture was concentrated to dryness and the residue was dissolved in 50 mL of H2O. The aqueous solution was adjusted to pH 8 by K2CO3 and was extracted with ethyl acetate. The crude product obtained upon concentration of the ethyl acetate extract was purified by flash silica gel column chromatography (hexane:ethyl acetate=1:1 elution). The desired compound was obtained as a thick colorless oil, 0.35 g.

후처리

  1. temperaturewas refluxed for 1 hour
  2. concentrationThe reaction mixture was concentrated to dryness
  3. dissolutionthe residue was dissolved in 50 mL of H2O
  4. extractionwas extracted with ethyl acetate
  5. customThe crude product obtained upon concentration of the ethyl acetate
  6. extractionextract
  7. customwas purified by flash silica gel column chromatography (hexane:ethyl acetate=1:1 elution)

출처 및 근거

ORD 기록
ord-5e23c20f06524ce8b50b4e5eb517db0f
출처 데이터셋
uspto-grants-1992_07
특허 번호
US05128355

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