5-Chloro-1H-indole-2-carboxylic acid → HCID 54012846, compound

HRID 651166Notes

Reaction equation

HRID 651166 reaction equation
Cl.[CH3:2][O:3][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].[Cl:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23]([C:28](O)=[O:29])=[CH:22]2>CN(C)C=O>[CH3:2][O:3][C:4](=[O:17])[C@@H:5]([NH:6][C:28]([C:23]1[NH:24][C:25]2[C:21]([CH:22]=1)=[CH:20][C:19]([Cl:18])=[CH:27][CH:26]=2)=[O:29])[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 826935-Chloro-1H-indole-2-carboxylic acidHCID 2734891Methyl tryptophanate hydrochloride

Product 1

HCID 54012846HCID 54012846, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

L-Tryptophan methyl ester hydrochloride (1.05 mmol) and 5-chloro-1H-indole-2-carboxylic acid (1.0 mmol) were coupled according to Procedure A (0-25° C., dimethyl-formamide reaction solvent) and the product purified by chromatography on silica gel eluted with 10%, 20%, 30%, 40%, 50% and 60% ethyl acetate-hexanes giving a yellow foam. Yield, 79%; HPLC (60/40) 7.43 minutes (96%);

Workup

  1. customthe product purified by chromatography on silica gel
  2. washeluted with 10%, 20%, 30%, 40%, 50% and 60% ethyl acetate-hexanes giving a yellow foam
  3. customYield

Sources & evidence

ORD record
ord-b9d7ebd1f4284a3db85e0436ba449541
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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