3(S)-[1-(4'-cyanobiphenyl-4-yl)-1H-pyrrol-3-yl]-N-(4,4-dimethyl-2-oxo-tetrahydrofuran-3(S)-yl)succinamic acid benzyl ester → 3(S)-[1-(4'-cyanobiphenyl-4-yl)-1H-pyrrol-3-yl]-N-(4, 4-dimethyl-2-oxo-tetrahydrofuran-3(S)-yl)succinamic acid

HRID 382197Notes

Reaction equation

HRID 382197 reaction equation
C([O:8][C:9](=[O:42])[CH2:10][C@@H:11]([C:23]1[CH:27]=[CH:26][N:25]([C:28]2[CH:33]=[CH:32][C:31]([C:34]3[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=3)=[CH:30][CH:29]=2)[CH:24]=1)[C:12]([NH:14][C@H:15]1[C:19]([CH3:21])([CH3:20])[CH2:18][O:17][C:16]1=[O:22])=[O:13])C1C=CC=CC=1>CCO.CCOC(C)=O>[C:40]([C:37]1[CH:38]=[CH:39][C:34]([C:31]2[CH:30]=[CH:29][C:28]([N:25]3[CH:26]=[CH:27][C:23]([C@@H:11]([C:12]([NH:14][C@H:15]4[C:19]([CH3:20])([CH3:21])[CH2:18][O:17][C:16]4=[O:22])=[O:13])[CH2:10][C:9]([OH:42])=[O:8])=[CH:24]3)=[CH:33][CH:32]=2)=[CH:35][CH:36]=1)#[N:41]

Participants

3

Reactant 1

HCID 599326853(S)-[1-(4'-cyanobiphenyl-4-yl)-1H-pyrrol-3-yl]-N-(4,4-dimethyl-2-oxo-tetrahydrofuran-3(S)-yl)succinamic acid benzyl ester

Product 1

HCID 98048113(S)-[1-(4'-cyanobiphenyl-4-yl)-1H-pyrrol-3-yl]-N-(4, 4-dimethyl-2-oxo-tetrahydrofuran-3(S)-yl)succinamic acidYield 81%

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

According to the procedure described in Example 1(a), 3(S)-[1-(4′-cyanobiphenyl-4-yl)-1H-pyrrol-3-yl]-N-(4, 4-dimethyl-2-oxo-tetrahydrofuran-3 (S)-yl)succinamic acid benzyl ester was hydrogenolyzed in EtOH/EtOAc for 3h to give a 81% yield of 3(S)-[1-(4′-cyanobiphenyl-4-yl)-1H-pyrrol-3-yl]-N-(4, 4-dimethyl-2-oxo-tetrahydrofuran-3(S)-yl)succinamic acid:

Sources & evidence

ORD record
ord-d998cab91a8e4ee9a2c07c5b25319b37
Source dataset
uspto-grants-2001_10
Patent number
US06306892B1

Reaction notes

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