Pyrrole → HCID 53797587, compound

HRID 1973490Notes

Reaction equation

HRID 1973490 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[CH:25]=[CH:24][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:22]1[NH:21][CH:25]=[CH:24][CH:23]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 8027PyrroleHCID 20312395HCID 20312395, compound

Product 1

HCID 53797587HCID 53797587, compound

Procedure

A solution of 14.5 g. (0.05 mol.) of N-t-butoxycarbonyl-2-acetoxyglycine n-butyl ester and 10 ml. of redistilled pyrrole in 75 ml. of toluene was slowly distilled with replacement of fresh toluene to maintain the volume at 50-75 ml. After 30 minutes the reaction mixture was cooled and concentrated in vacuo. The residue was dissolved in hexane and chromatographed on alumina (Woelm, activity II) with hexane-benzene followed by benzene to give the title compound.

Workup

  1. distillationof toluene was slowly distilled with replacement of fresh toluene
  2. temperatureto maintain the volume at 50-75 ml
  3. temperatureAfter 30 minutes the reaction mixture was cooled
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in hexane
  6. customchromatographed on alumina (Woelm, activity II) with hexane-benzene

Sources & evidence

ORD record
ord-b44c8ac498dd494da9f9324e3d89ddc8
Source dataset
uspto-grants-1976_12
Patent number
US03997584

Reaction notes

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