Anisole → 3-(6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-2-methoxypyridin-3-yl)propanoic acid

HRID 70668Notes

Reaction equation

C1(OC)C=CC=CC=1.[C:9]([C:13]1[CH:18]=[CH:17][C:16](/[C:19](/[C:38]2[N:43]=[C:42]([O:44][CH3:45])[C:41]([CH2:46][CH2:47][C:48]([O:50]C(C)(C)C)=[O:49])=[CH:40][CH:39]=2)=[CH:20]\[C@H:21]2[CH2:25][CH2:24][C:23](=[O:26])[N:22]2[CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=2[O:36][CH3:37])=[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[N:43]=[C:42]([O:44][CH3:45])[C:41]([CH2:46][CH2:47][C:48]([OH:50])=[O:49])=[CH:40][CH:39]=2)=[CH:20]\[C@H:21]2[CH2:25][CH2:24][C:23](=[O:26])[N:22]2[CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=2[O:36][CH3:37])=[CH:15][CH:14]=1)([CH3:12])([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 65 °C

Procedure

Anisole (1 mL) was added to a solution of tert-butyl 3-(6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-2-methoxypyridin-3-yl)propanoate (293 mg) in trifluoroacetic acid (2 mL), and the mixture was stirred at 65° C. for two hours. The solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=1:0→9:1) to give 3-(6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-2-methoxypyridin-3-yl)propanoic acid as a colorless amorphous (172 mg).

Workup

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

Sources & evidence

ORD record: ord-8fa4cbbee0f04b23906db1ad9a5c9f20
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822503B2

Reaction notes

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