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

HRID 882829Notes

Reaction equation

HRID 882829 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][N:6]1[C:10](=[O:11])[CH2:9][CH2:8][C@@H:7]1[C:12]([OH:14])=O.[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:12]([C@H:7]1[CH2:8][CH2:9][C:10](=[O:11])[N:6]1[CH2:5][C:4]1[CH:15]=[CH:16][CH:17]=[C:2]([F:1])[CH:3]=1)=[O:14])[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 67094846(R)-1-(3-fluoro-benzyl)-5-oxo-pyrrolidine-2-carboxylic acidHCID 178514248HCID 178514248, compound

Product 1

HCID 67095122(2R)-N-(4-Amino-3,4-dioxo-1-phenylbutan-2-yl)-1-(3-fluorobenzyl)-5-oxopyrrolidine-2-carboxamide

Procedure

Coupling of (R)-1-(3-fluoro-benzyl)-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-da3ff0c8e42549118ab0df211e8cc325
Source dataset
uspto-grants-2012_08
Patent number
US08236798B2

Reaction notes

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