Nitrate(1-), oxo- → (2R,4S)-N-(4-Amino-3,4-dioxo-1-phenylbutan-2-yl)-1-benzyl-4-methyl-5-oxopyrrolidine-2-carboxamide

HRID 882840Notes

Reaction equation

HRID 882840 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[C@@H:11]([CH3:14])[CH2:10][C@@H:9]1[C:15]([OH:17])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:18][CH:19]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH:20]([OH:24])[C:21]([NH2:23])=[O:22].O[NH-].O=[N-]>>[NH2:23][C:21](=[O:22])[C:20](=[O:24])[CH:19]([NH:18][C:15]([C@H:9]1[CH2:10][C@H:11]([CH3:14])[C:12](=[O:13])[N:8]1[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:17])[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 4

HCID 3001380Nitrate(1-), oxo-HCID 138823553-Amino-2-hydroxy-4-phenylbutanamideHCID 66644841(2R,4S)-1-Benzyl-4-methyl-5-oxo-pyrrolidine-2-carboxylic AcidHCID 178514248HCID 178514248, compound

Product 1

HCID 66644846(2R,4S)-N-(4-Amino-3,4-dioxo-1-phenylbutan-2-yl)-1-benzyl-4-methyl-5-oxopyrrolidine-2-carboxamide

Procedure

Coupling of (2R,4S)-1-Benzyl-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid with 3-amino-2-hydroxy-4-phenylbutanamide and oxidation of the resulting hydroxyamide intermediate to the corresponding ketoamide.

Sources & evidence

ORD record
ord-25b0d7d5328e48939ceb0397cd0d62fa
Source dataset
uspto-grants-2012_08
Patent number
US08236798B2

Reaction notes

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