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

HRID 1474119Notes

Reaction equation

HRID 1474119 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[C:11](=[O:12])[CH2:10][CH2:9][C@@H:8]2[C:13]([OH:15])=O)=[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:13]([C@H:8]1[CH2:9][CH2:10][C:11](=[O:12])[N:7]1[CH2:6][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:17][CH:16]=1)=[O:15])[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 40516921(R)-1-(4-fluoro-benzyl)-5-oxo-pyrrolidine-2-carboxylic acidHCID 178514248HCID 178514248, compound

Product 1

HCID 67095120(2R)-N-(4-Amino-3,4-dioxo-1-phenylbutan-2-yl)-1-(4-fluorobenzyl)-5-oxopyrrolidine-2-carboxamide

Procedure

Coupling of (R)-1-(4-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-0149741e298440908c5d82e285833159
Source dataset
uspto-grants-2015_04
Patent number
US09018206B2

Reaction notes

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