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

HRID 882830Notes

Reaction equation

HRID 882830 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:19]=[CH:18][CH:17]=[CH:16][C:5]=1[CH2:6][N:7]1[C:11](=[O:12])[CH2:10][CH2:9][C@@H:8]1[C:13]([OH:15])=O.[NH2:22][CH:23]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:24]([OH:28])[C:25]([NH2:27])=[O:26].O[NH-].O=[N-]>>[NH2:27][C:25](=[O:26])[C:24](=[O:28])[CH:23]([NH:22][C:13]([C@H:8]1[CH2:9][CH2:10][C:11](=[O:12])[N:7]1[CH2:6][C:5]1[CH:16]=[CH:17][CH:18]=[CH:19][C:4]=1[O:3][C:2]([F:1])([F:21])[F:20])=[O:15])[CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 4

HCID 3001380Nitrate(1-), oxo-HCID 138823553-Amino-2-hydroxy-4-phenylbutanamideHCID 66645103(R)-1-(2-trifluoromethoxy-benzyl)-5-oxo-pyrrolidine-2-carboxylic acidHCID 178514248HCID 178514248, compound

Product 1

HCID 66644766(2R)-N-(4-Amino-3,4-dioxo-1-phenylbutan-2-yl)-5-oxo-1-[2-(trifluoromethoxy)-benzyl]pyrrolidine-2-carboxamide

Procedure

Coupling of (R)-1-(2-trifluoromethoxy-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-d72724982a0a4e88b64fa80df1e78e91
Source dataset
uspto-grants-2012_08
Patent number
US08236798B2

Reaction notes

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