Methyl tryptophanate hydrochloride → {3-[4-(Aminoiminomethyl)benzyl]-2,5-dioxopyrrolidin-1-yl}acetyl-L-tryptophan methyl ester

HRID 2257996Notes

Reaction equation

HRID 2257996 reaction equation
Cl.[NH2:2][N:3]=[CH:4][C:5]1[CH:22]=[CH:21][C:8]([CH2:9][CH:10]2[CH2:14][C:13](=[O:15])[N:12]([CH2:16][C:17]([OH:19])=O)[C:11]2=[O:20])=[CH:7][CH:6]=1.Cl.[CH3:24][O:25][C:26](=[O:39])[C@H:27]([CH2:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[NH:32][CH:31]=1)[NH2:28]>>[CH3:24][O:25][C:26](=[O:39])[C@H:27]([CH2:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[NH:32][CH:31]=1)[NH:28][C:17](=[O:19])[CH2:16][N:12]1[C:13](=[O:15])[CH2:14][CH:10]([CH2:9][C:8]2[CH:7]=[CH:6][C:5]([CH:4]=[N:3][NH2:2])=[CH:22][CH:21]=2)[C:11]1=[O:20]

Participants

3

Reactant 2

HCID 2734891Methyl tryptophanate hydrochlorideHCID 67725476{3-[4-(Aminoiminomethyl)benzyl]-2,5-dioxopyrrolidin-1-yl}acetic acid hydrochloride

Product 1

HCID 67725084{3-[4-(Aminoiminomethyl)benzyl]-2,5-dioxopyrrolidin-1-yl}acetyl-L-tryptophan methyl ester

Procedure

403 mg of {3-[4-(aminoiminomethyl)benzyl]-2,5-dioxopyrrolidin-1-yl}acetic acid hydrochloride are coupled with 356.6 mg of L-tryptophan methyl ester hydrochloride by the process described above. After working up and chromatographic purification, 270 mg of {3-[4-(aminoiminomethyl)benzyl]-2,5-dioxopyrrolidin-1-yl}acetyl-L-tryptophan methyl ester are obtained.

Workup

  1. customchromatographic purification, 270 mg of {3-[4-(aminoiminomethyl)benzyl]-2,5-dioxopyrrolidin-1-yl}acetyl-L-tryptophan methyl ester
  2. customare obtained

Sources & evidence

ORD record
ord-bee2b9cf96774dff826f9c69d08b8b96
Source dataset
uspto-grants-1997_08
Patent number
US05658935

Reaction notes

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