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

HRID 2257999Notes

Reaction equation

HRID 2257999 reaction equation
C[O:2][C:3](=[O:36])[C@H:4]([CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1)[NH:5][C:6](=[O:25])[CH2:7][N:8]1[C:12](=[O:13])[CH2:11][CH:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]=[N:22][NH2:23])=[CH:17][CH:16]=2)[C:9]1=[O:24]>Cl>[NH2:23][N:22]=[CH:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH:10]2[CH2:11][C:12](=[O:13])[N:8]([CH2:7][C:6]([NH:5][C@H:4]([C:3]([OH:36])=[O:2])[CH2:26][C:27]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[NH:29][CH:28]=3)=[O:25])[C:9]2=[O:24])=[CH:16][CH:17]=1

Participants

3

Reactant 1

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

Product 1

HCID 67725592{3-[4-(aminoiminomethyl)benzyl]-2,5-dioxopyrrolidin-1-yl}acetyl-L-tryptophanYield 34.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

204 mg of {3-[4-(aminoiminomethyl)benzyl]-2,5-dioxopyrrolidin-1-yl}acetyl-L-tryptophan methyl ester are heated with 10 ml of 6N HCl for 3 min, then the mixture is evaporated to dryness and the residue is redistilled twice with water. The residue is taken up in a little water and freeze-dried. 68 mg of {3-[4-(aminoiminomethyl)benzyl]-2,5-dioxopyrrolidin-1-yl}acetyl-L-tryptophan are obtained.

Workup

  1. customthe mixture is evaporated to dryness
  2. distillationthe residue is redistilled twice with water
  3. customfreeze-dried

Sources & evidence

ORD record
ord-ee663454a67149fc84fc032185ac8f05
Source dataset
uspto-grants-1997_08
Patent number
US05658935

Reaction notes

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