Water → HCID 67399711, compound

HRID 70640Notes

Reaction equation

O.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[C:16]([C:20]1[CH:25]=[CH:24][C:23](/[C:26](/[C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[C:47]([O:53]CC3C=CC(OC)=CC=3)[N:46]=2)=[CH:27]\[C@@H:28]2[N:32]([CH2:33][C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:35]=3[O:42][CH3:43])[C:31](=[O:44])[CH2:30][CH2:29]2)=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17]>C(Cl)(Cl)Cl>[C:16]([C:20]1[CH:21]=[CH:22][C:23](/[C:26](/[C:45]2[NH:46][C:47](=[O:53])[C:48]([O:51][CH3:52])=[CH:49][CH:50]=2)=[CH:27]\[C@H:28]2[CH2:29][CH2:30][C:31](=[O:44])[N:32]2[CH2:33][C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:35]=2[O:42][CH3:43])=[CH:24][CH:25]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 65 °C

Procedure

Water (0.2 mL) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (72 mg) were added to a solution of (5R)-5-[(E)-2-(4-tert-butylphenyl)-2-{5-methoxy-6-[(4-methoxybenzyl)oxy]-pyridin-2-yl}ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one (202 mg) in chloroform (4 mL), and the mixture was stirred at 65° C. for 21 hours. Chloroform was added. After filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=1:0→95:5 9:1) to give 6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-3-methoxypyridin-2(1H)-one (65 mg).

Workup

filtrationAfter filtration
customthe solvent was evaporated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=1:0→95:5 9:1)

Sources & evidence

ORD record: ord-f0d6077fd2634ab992b6b6753c68aa16
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822503B2

Reaction notes

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