Indole → HCID 53919156, compound

HRID 1973484Notes

Reaction equation

HRID 1973484 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 minute 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 minute 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-05bb3eaeed48415fad7579a733877df7
Source dataset
uspto-grants-1976_12
Patent number
US03997584

Reaction notes

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