Sodium Hydroxide → (Z)-2-benzylidene-3-(cis-hexahydro-2-isoindolinylcarbonyl)propionic acid

反応式

[CH:1](=[C:8]1/[C:9]([O:11][C:12](=[O:14])[CH2:13]/1)=[O:10])/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]1[C@@H:23]2[C@@H:18]([CH2:19][CH2:20][CH2:21][CH2:22]2)[CH2:17][NH:16]1.[OH-].[Na+]>ClCCl>[CH:1](=[C:8](/[CH2:13][C:12]([N:16]1[CH2:17][C@H:18]2[C@H:23]([CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:15]1)=[O:14])\[C:9]([OH:11])=[O:10])\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

実験手順

To a suspension of (Z)-benzylidenesuccinic anhydride (139 mg) in dichloromethane (30 ml) was added cis-hexahydroisoindoline (120 mg) and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added 2N sodium hydroxide solution and the mixture was extracted with diethyl ether. The aqueous layer was acidified with 1N hydrochloric acid and extracted with dichloromethane. The organic layer was washed with brine and dried over MgSO4. After the solvent was evaporated under reduced pressure, the residue was crystallized from ethyl acetate to give 190 mg of (Z)-2-benzylidene-3-(cis-hexahydro-2-isoindolinylcarbonyl)propionic acid.