Nitrate(1-), oxo- → (2R)-N-(4-Amino-3,4-dioxo-1-phenylbutan-2-yl)-5-oxo-1-[2-methoxy-6-(trifluoromethyl)benzyl]pyrrolidine-2-carboxamide

HRID 2061685Notes

Reaction equation

HRID 2061685 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][C:9]=2[O:18][CH3:19])[C@@H:5]([C:20]([OH:22])=O)[CH2:4][CH2:3]1.[NH2:23][CH:24]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH:25]([OH:29])[C:26]([NH2:28])=[O:27].O[NH-].O=[N-]>>[NH2:28][C:26](=[O:27])[C:25](=[O:29])[CH:24]([NH:23][C:20]([C@H:5]1[CH2:4][CH2:3][C:2](=[O:1])[N:6]1[CH2:7][C:8]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][C:9]=1[O:18][CH3:19])=[O:22])[CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 4

HCID 3001380Nitrate(1-), oxo-HCID 138823553-Amino-2-hydroxy-4-phenylbutanamideHCID 66644853(R)-1-(2-methoxy-6-(trifluoromethyl)benzyl)-5-oxopyrrolidine-2-carboxylic acidHCID 178514248HCID 178514248, compound

Product 1

HCID 46944251(2R)-N-(4-Amino-3,4-dioxo-1-phenylbutan-2-yl)-5-oxo-1-[2-methoxy-6-(trifluoromethyl)benzyl]pyrrolidine-2-carboxamide

Procedure

Coupling of (R)-5-oxo-1-(2-methoxy-6-trifluoromethyl-benzyl)-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-63e58b8c4eb1458e8349ff2c6727471f
Source dataset
uspto-grants-2012_10
Patent number
US08283363B2

Reaction notes

Loading…