Ammonia → 3-(6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-2-oxo-1,2-dihydropyridin-3-yl)propanamide

HRID 70670Notes

Reaction equation

HRID 70670 reaction equation
C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[C:13]([C:17]1[CH:22]=[CH:21][C:20](/[C:23](/[C:42]2[NH:47][C:46](=[O:48])[C:45]([CH2:49][CH2:50][C:51]([OH:53])=O)=[CH:44][CH:43]=2)=[CH:24]\[C@H:25]2[CH2:29][CH2:28][C:27](=[O:30])[N:26]2[CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][C:33]=2[O:40][CH3:41])=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14].N>O1CCCC1>[C:13]([C:17]1[CH:22]=[CH:21][C:20](/[C:23](/[C:42]2[NH:47][C:46](=[O:48])[C:45]([CH2:49][CH2:50][C:51]([NH2:3])=[O:53])=[CH:44][CH:43]=2)=[CH:24]\[C@H:25]2[CH2:29][CH2:28][C:27](=[O:30])[N:26]2[CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][C:33]=2[O:40][CH3:41])=[CH:19][CH:18]=1)([CH3:14])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 67396240HCID 67396240, compound

Product 1

HCID 673987563-(6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-2-oxo-1,2-dihydropyridin-3-yl)propanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1′-Carbonyldiimidazole (24.8 mg) was added to a solution of 3-(6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-2-oxo-1,2-dihydropyridin-3-yl)propanoic acid (77.8 mg) in tetrahydrofuran (1.6 mL). 28% aqueous ammonia (0.2 mL) was further added, followed by stirring for 15 hours. The reaction system was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1) to give 3-(6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-2-oxo-1,2-dihydropyridin-3-yl)propanamide as a colorless amorphous (82.6 mg).

Workup

  1. concentrationThe reaction system was concentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1)

Sources & evidence

ORD record
ord-1f21d57a701e45f1ad9a82905285628b
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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