Indole → HCID 53919156, compound

HRID 1731040Notes

Reaction equation

HRID 1731040 reaction equation
[CH2:1]([O:5][C:6](=[O:20])[CH:7](OC(=O)C)[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:2][CH2:3][CH3:4].[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22]1>>[CH2:1]([O:5][C:6](=[O:20])[CH:7]([NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[C:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[NH:21][CH:22]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 798IndoleHCID 20312395HCID 20312395, compound

Product 1

HCID 53919156HCID 53919156, compound

Procedure

A solution of 20.2 g. (0.070 mol.) of N-t-butoxycarbonyl-2-acetoxyglycine n-butyl ester and 8.8 g. (0.075 mol.) of indole in 300 ml. of toluene was slowly distilled over a 30 minutes interval with periodic replacement of the toluene with fresh solvent. After an additional 45 minutes the reaction mixture was cooled and the solvent was evaporated in vacuo. The residue was triturated with hexane to give α-(N-t-butoxycarbonylamino)indole-3-acetic acid n-butyl ester, m.p. 127°-128° (ether-hexane).

Workup

  1. distillationof toluene was slowly distilled over a 30 minutes interval with periodic replacement of the toluene with fresh solvent
  2. temperatureAfter an additional 45 minutes the reaction mixture was cooled
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-8e20fb3c68a94e99a45c6de9dd1c0784
Source dataset
uspto-grants-1976_11
Patent number
US03994954

Reaction notes

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