N-methyl-3(R)-[3-[4-(pyndin-4-yl)phenyl]-1H-pyrrol-1-yl]succinamic acid benzyl ester → N-methyl-3(R)-[3-[4-(pyridin-4-yl)phenyl]-1H-pyrrol-1-yl]succinamic acid

HRID 613895Notes

Reaction equation

HRID 613895 reaction equation
C([O:8][C:9](=[O:33])[CH2:10][C@@H:11]([N:16]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)=[CH:23][CH:22]=2)=[CH:17]1)[C:12]([NH:14][CH3:15])=[O:13])C1C=CC=CC=1>C(O)(=O)C>[CH3:15][NH:14][C:12](=[O:13])[C@H:11]([N:16]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:28]=[CH:29][N:30]=[CH:31][CH:32]=3)=[CH:23][CH:22]=2)=[CH:17]1)[CH2:10][C:9]([OH:33])=[O:8]

Participants

3

Reactant 1

HCID 53874083N-methyl-3(R)-[3-[4-(pyndin-4-yl)phenyl]-1H-pyrrol-1-yl]succinamic acid benzyl ester

Product 1

HCID 54315845N-methyl-3(R)-[3-[4-(pyridin-4-yl)phenyl]-1H-pyrrol-1-yl]succinamic acidYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

According to the procedure described in Example 7(a), N-methyl-3(R)-[3-[4-(pyridin-4-yl)phenyl]-1H-pyrrol-1-yl]succinamic acid benzyl ester was hydrogenolyzed in acetic acid to yield in 90% yield N-methyl-3(R)-[3-[4-(pyridin-4-yl)phenyl]-1H-pyrrol-1-yl]succinamic acid as a yellow amorphous solid. 1HNMR (DMSO-d6): δ 8.58 (d, 2H, J=5.9 Hz), 7.75 (d, 2H, J=8.1 Hz), 7.71 (d, 2H, J=6.2 Hz), 7.61 (d, 2H, J=8.4 Hz), 7.29 (s, 1H), 6.77 (t, 1H, J=2.2 Hz), 6.42 (t, 1H, J=2.2 Hz), 4.80 (d, 1H, J=10.7 Hz), 3.16 (dd, 1H, J=15.8, 11.0 Hz), 2.36 (s, 3H). Anal. Calculated for C20H19N3O3.1.0 H2O.0.33 AcOH: C, 64.08; H, 5.81; N, 10.85. Found: C, 64.23, 64.16; H, 5.66, 5.67; N, 10.83, 10.78.

Sources & evidence

ORD record
ord-3e43dfe638694467b1609e4e4f18ffb9
Source dataset
uspto-grants-1999_12
Patent number
US06008243

Reaction notes

Loading…