N-(2,2-dimethyl-1(S)-(methylcarbamoyl)propyl)-3(R)-[3-(4-(pyridin-4-yl)phenyl)-1H-pyrrol-1-yl]succinamic acid benzyl ester → N-(2,2-dimethyl-1(S)-(methylcarbamoyl)propyl)-3(R)-[3-(4-(pyridin-4-yl)phenyl)-1H-pyrrol-1-yl]succinamic acid

HRID 566784Notes

Reaction equation

HRID 566784 reaction equation
C([O:8][C:9](=[O:41])[CH2:10][C@@H:11]([N:24]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=3)=[CH:31][CH:30]=2)=[CH:25]1)[C:12]([NH:14][C@H:15]([C:20](=[O:23])[NH:21][CH3:22])[C:16]([CH3:19])([CH3:18])[CH3:17])=[O:13])C1C=CC=CC=1>CO>[CH3:17][C:16]([CH3:19])([CH3:18])[C@H:15]([NH:14][C:12](=[O:13])[C@H:11]([N:24]1[CH:28]=[CH:27][C:26]([C:29]2[CH:30]=[CH:31][C:32]([C:35]3[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=3)=[CH:33][CH:34]=2)=[CH:25]1)[CH2:10][C:9]([OH:41])=[O:8])[C:20](=[O:23])[NH:21][CH3:22]

Participants

3

Reactant 1

HCID 53931309N-(2,2-dimethyl-1(S)-(methylcarbamoyl)propyl)-3(R)-[3-(4-(pyridin-4-yl)phenyl)-1H-pyrrol-1-yl]succinamic acid benzyl ester

Product 1

HCID 53964311N-(2,2-dimethyl-1(S)-(methylcarbamoyl)propyl)-3(R)-[3-(4-(pyridin-4-yl)phenyl)-1H-pyrrol-1-yl]succinamic acidYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to the procedure described in Example 1(a), N-(2,2-dimethyl-1(S)-(methylcarbamoyl)propyl)-3(R)-[3-(4-(pyridin-4-yl)phenyl)-1H-pyrrol-1-yl]succinamic acid benzyl ester was hydrogenolyzed in MeOH after 20 hours. Purification via flash column chromatography with 1% HOAc/10% MeOH/CHCl3 as eluant and azeotrope with n-heptane furnished 24 mg (32%) of N-(2,2-dimethyl-1(S)-(methylcarbamoyl)propyl)-3(R)-[3-(4-(pyridin-4-yl)phenyl)-1H-pyrrol-1-yl]succinamic acid as yellow crystals. 1H NMR (CD3OD): δ 8.54 (d, 2H, J=5.6 Hz), 7.99 (bd, 1H, J=4.4 Hz), 7.80-7.59 (m, 6H), 7.34 (t, 1H, J=1.9 Hz), 6.92 (t, 1H, J=2.5 Hz), 6.55 (dd, 1H, J=1.9, 2.8 Hz), 5.28 (t, 1H, J=7.2 Hz), 4.17 (s, 1H), 3.23 (dd, 1H, J=7.5, 16.7 Hz), 3.01 (dd, 1H, J=7.2, 16.7 Hz), 2.66 (d, 3H, J=3.5 Hz), 0.95 (s, 9H). IR(KBr): 3422, 1654, 1598, 1562, 1535 cm−1. HRFABMS: Calculated for C26H31N4O4(M+H+): 463.2345. Found: 463.2356. Anal. Calculated for C26H30N4O4•1.15 H2O•0.1 CHCl3: C, 63.30; H, 6.59; N, I 1.31. Found: C, 63.28; H, 6.58; N, 11.08.

Workup

  1. customPurification via flash column chromatography with 1% HOAc/10% MeOH/CHCl3 as eluant

Sources & evidence

ORD record
ord-99852a5742374a2e8987a167db612ed6
Source dataset
uspto-grants-2001_01
Patent number
US06174915B1

Reaction notes

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