Indole-2-carboxylic acid → cis-4-[(1H-Indol-2-ylcarbonyl)amino]-5-oxo-1-phenyl-3-pyrrolidineacetic acid

HRID 1590264Notes

Reaction equation

HRID 1590264 reaction equation
O[N:2]=[C:3]1[C:7](=[O:8])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH:4]1[CH2:15][C:16]([O:18]CC)=[O:17].[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[C:22]1[C:30](O)=[O:31]>>[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[C:22]1[C:30]([NH:2][C@H:3]1[C:7](=[O:8])[N:6]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:5][C@H:4]1[CH2:15][C:16]([OH:18])=[O:17])=[O:31]

Participants

3

Reactant 2

HCID 72899Indole-2-carboxylic acidHCID 86746704Ethyl 4-(hydroxyimino)-5-oxo-1-phenyl-3-pyrrolidineacetate

Product 1

HCID 67795074cis-4-[(1H-Indol-2-ylcarbonyl)amino]-5-oxo-1-phenyl-3-pyrrolidineacetic acid

Procedure

The aminopyrrolidinone of Example 63 is coupled with indole-2-carboxylic acid according to the procedure described in Example 4 and the resulting ester is saponified to give the title homologated acid.

Workup

  1. customto give the title homologated acid

Sources & evidence

ORD record
ord-cda35a46ba3e44f6af0d869886fa1f1b
Source dataset
uspto-grants-1993_04
Patent number
US05202344

Reaction notes

Loading…