Ethylamine → (2R)-1-Benzyl-N-[4-(ethylamino)-3,4-dioxo-1-phenylbutan-2-yl]-5-oxopyrrolidine-2-carboxamide

HRID 882845Notes

Reaction equation

HRID 882845 reaction equation
C(N1[C:12](=[O:13])[CH2:11][CH2:10][C@@H:9]1[C:14]([NH:16][CH:17]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:18]([OH:22])[C:19]([OH:21])=O)=[O:15])C1C=CC=CC=1.[CH2:30]([NH2:32])[CH3:31].O[NH-].O=[N-]>>[CH2:30]([N:32]1[C:12](=[O:13])[CH2:11][CH2:10][C@@H:9]1[C:14]([NH:16][CH:17]([C:18](=[O:22])[C:19]([NH:16][CH2:14][CH3:9])=[O:21])[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:15])[C:31]1[CH:24]=[CH:23][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 4

HCID 6341EthylamineHCID 3001380Nitrate(1-), oxo-HCID 666445723-((R)-1-Benzyl-5-oxopyrrolidine-2-carboxamido)-2-hydroxy-4-phenylbutanoic AcidHCID 178514248HCID 178514248, compound

Product 1

HCID 67094752(2R)-1-Benzyl-N-[4-(ethylamino)-3,4-dioxo-1-phenylbutan-2-yl]-5-oxopyrrolidine-2-carboxamide

Procedure

Coupling of 3-((R)-1-benzyl-5-oxopyrrolidine-2-carboxamido)-2-hydroxy-4-phenyl-butanoic acid with ethylamine and oxidation of the resulting hydroxyamide intermediate to the corresponding ketoamide.

Sources & evidence

ORD record
ord-ed219dc37f4241f0a6d14b44cfd8296c
Source dataset
uspto-grants-2012_08
Patent number
US08236798B2

Reaction notes

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