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 613919Notes

Reaction equation

HRID 613919 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 3 h 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: 1HNMR (DMSO-d6): δ 12.2 (bs, 1H), 8.48 (d, 1H, J=8.8 Hz), 7.92 (s, 4H), 7.86 (d, 2H, J=8.5 Hz), 7.67 (d, 2H, J=8.5 Hz), 7.40 (s, 1H), 7.37 (s, 1H), 6.33 (s, 1H), 4.75 (d, 1H, J=8.8 Hz), 4.08, 4.00 (AB quartet, 2H, J=8.6 Hz), 3.97-3.92 (m, 1H), 3.01-2.92 (m, 1H), 2.64 (dd, 1H, J=16.54, 4.0 Hz), 1.05 (s, 3H), 0.97 (s, 3H); Anal. Calculated for C27H25N3O5.C5H12O (MTBE): C, 68.67; H, 6.66; N, 7.51. Found: 69.00, 68.91; H, 6.42; N, 7.60, 7.52.

Sources & evidence

ORD record
ord-7a55e134a6ff461789171177188a3986
Source dataset
uspto-grants-1999_12
Patent number
US06008243

Reaction notes

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