4-Methoxy-3-hydroxy-2-nitrobutyric acid ethyl ester → 3-(4-Acetoxymethylindol-3-yl)-2-nitro-4-methoxy-butyric acid ethyl ester

HRID 569078

반응식

HRID 569078 반응식
[C:1]([O:4][CH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2)(=[O:3])[CH3:2].[CH2:15]([O:17][C:18](=[O:28])[CH:19]([N+:25]([O-:27])=[O:26])[CH:20](O)[CH2:21][O:22][CH3:23])[CH3:16]>C1(C)C=CC=CC=1.C(O)(=O)C>[CH2:15]([O:17][C:18](=[O:28])[CH:19]([N+:25]([O-:27])=[O:26])[CH:20]([C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[CH:14][C:6]=2[CH2:5][O:4][C:1](=[O:3])[CH3:2])[NH:10][CH:9]=1)[CH2:21][O:22][CH3:23])[CH3:16]

참가 물질

5

반응물 2

HCID 131339864-Methoxy-3-hydroxy-2-nitrobutyric acid ethyl esterHCID 201323834-Acetoxymethylindole

생성물 1

HCID 542935723-(4-Acetoxymethylindol-3-yl)-2-nitro-4-methoxy-butyric acid ethyl ester

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 1140Toluene용매

실험 절차

4-Acetoxymethylindole (189 g) is dissolved in a mixture of toluene (6 l) and acetic acid (0.7 l). To this solution is added 3-hydroxy-2-nitro-5-oxa-hexanoic acid ethyl ester (570 ml). The flask containing the mixture is evacuated by means of a water jet pump. Then balancing to normal pressure is brought about by argon. Evacuation and pressure balancing are repeated four times. Then the reaction mixture is refluxed for two hours in a water-free argon atmosphere. After concentrating to 2 l the solution is diluted with ethyl acetate and shaken out three times with a liter of 1N hydrochloric acid each. Then it is washed to neutrality with saturated hydrochloric acid solution. The solution, dried over sodium sulfate, is evaporated. The residue is chromatographed on silica gel with dicloromethane. 393 g of the title compound is obtained in oily form.

후처리

  1. additionThe flask containing the mixture
  2. customis evacuated by means of a water jet pump
  3. temperatureThen the reaction mixture is refluxed for two hours in a water-free argon atmosphere
  4. concentrationAfter concentrating to 2 l the solution
  5. additionis diluted with ethyl acetate
  6. washThen it is washed to neutrality with saturated hydrochloric acid solution
  7. dry with materialThe solution, dried over sodium sulfate
  8. customis evaporated
  9. customThe residue is chromatographed on silica gel with dicloromethane

출처 및 근거

ORD 기록
ord-28aff600685b425abcbf35c0ea92f9de
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04731365

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