Anisole → 6-{(E)-1-(4-tert-Butylphenyl)-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-methoxypyridin-2(1H)-one

HRID 70641Notes

Reaction equation

C1(OC)C=CC=CC=1.[C:9]([C:13]1[CH:18]=[CH:17][C:16](/[C:19](/[C:38]2[NH:43][C:42](=[O:44])[C:41]([O:45][CH3:46])=[CH:40][CH:39]=2)=[CH:20]\[C@H:21]2[CH2:25][CH2:24][C:23](=[O:26])[N:22]2CC2C=CC(OC)=CC=2OC)=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10]>FC(F)(F)C(O)=O>[C:9]([C:13]1[CH:18]=[CH:17][C:16](/[C:19](/[C:38]2[NH:43][C:42](=[O:44])[C:41]([O:45][CH3:46])=[CH:40][CH:39]=2)=[CH:20]\[C@H:21]2[CH2:25][CH2:24][C:23](=[O:26])[NH:22]2)=[CH:15][CH:14]=1)([CH3:12])([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 80 °C

Procedure

Anisole (1 mL) was added to a solution of 6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-3-methoxypyridin-2(1H)-one (65 mg) in trifluoroacetic acid (2 mL), and the mixture was stirred at 80° C. for nine hours. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=1:0→9:1) to give the title compound as a colorless powder (29 mg).

Workup

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

Sources & evidence

ORD record: ord-ad12ff4183154705a7f494a4919673ac
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822503B2

Reaction notes

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