Methyl 2-amino-4-phenylbutanoate → {3-[4-(Aminoiminomethyl)benzyl]-2,5-dioxopyrrolidin-1-yl}acetyl-D,L-homophenylalanine methyl ester

HRID 2257997Notes

Reaction equation

HRID 2257997 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.[CH3:23][O:24][C:25](=[O:36])[CH:26]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[NH2:27]>>[CH3:23][O:24][C:25](=[O:36])[CH:26]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[NH:27][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 10856340Methyl 2-amino-4-phenylbutanoateHCID 67725476{3-[4-(Aminoiminomethyl)benzyl]-2,5-dioxopyrrolidin-1-yl}acetic acid hydrochloride

Product 1

HCID 131720120{3-[4-(Aminoiminomethyl)benzyl]-2,5-dioxopyrrolidin-1-yl}acetyl-D,L-homophenylalanine methyl ester

Procedure

403 mg of {3-[4-(aminoiminomethyl)benzyl]-2,5-dioxopyrrolidin-1-yl}acetic acid hydrochloride are coupled with 270 mg of D,L-homophenylalanine methyl ester by the process described above. After working up and chromatographic purification, 343 mg of {3-[4-(aminoiminomethyl)benzyl]-2,5-dioxopyrrolidin-1-yl}-acetyl-D,L-homophenylalanine methyl ester are obtained.

Workup

  1. customchromatographic purification, 343 mg of {3-[4-(aminoiminomethyl)benzyl]-2,5-dioxopyrrolidin-1-yl}-acetyl-D,L-homophenylalanine methyl ester
  2. customare obtained

Sources & evidence

ORD record
ord-3f26847c2d1a4fae90761114ffb2b40b
Source dataset
uspto-grants-1997_08
Patent number
US05658935

Reaction notes

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