Pyridine → L-Tryptophanamide

HRID 1276591Notes

Reaction equation

HRID 1276591 reaction equation
Cl.CO[C:4](=[O:17])[C@H:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[NH2:6].[N:18]1C=CC=CC=1>ClCCl>[NH2:6][C@H:5]([C:4]([NH2:18])=[O:17])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 2734891Methyl tryptophanate hydrochloride

Product 1

HCID 439356L-Tryptophanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the active ester VIII (0.035 g, 0.06 mmol), L-tryptophan methyl ester hydrochloride (0.049 g, 0.19 mmol) and pyridine (0.015 g, 0.19 mmol) in dichloromethane (20 ml) was stirred overnight. The solvent was removed under reduced pressure and the residue purified by column chromatography (ethyl acetate elution) to yield the trytophan amide as a dark red crystalline solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by column chromatography (ethyl acetate elution)

Sources & evidence

ORD record
ord-1b4fd1c1137a43baa4c47018ac7cf7d7
Source dataset
uspto-grants-2000_12
Patent number
US06166202

Reaction notes

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