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

HRID 845231

Reaction equation

HRID 845231 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

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 dichloromethane. 393 g of the title compound is obtained in oily form.

Workup

  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 dichloromethane

Sources & evidence

ORD record
ord-a457c7c2d7da4d5f830c81a6a2ff9ef6
Source dataset
uspto-grants-1988_07
Patent number
US04757070

Linked notes

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