Lithium Hydroxide → Imidazo(1,2-a)pyridine-6-carboxylic acid, 3-(2-(dimethylamino)-2-oxoethyl)-2-(4-methylphenyl)-

反応式

[OH-].[Li+].[CH3:3][N:4]([CH3:28])[C:5]([CH2:7][C:8]1[N:12]2[CH:13]=[C:14]([C:17]([O:19]C)=[O:18])[CH:15]=[CH:16][C:11]2=[N:10][C:9]=1[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)=[O:6]>O1CCCC1.C(Cl)(Cl)Cl.CO>[CH3:28][N:4]([CH3:3])[C:5]([CH2:7][C:8]1[N:12]2[CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=[CH:16][C:11]2=[N:10][C:9]=1[C:21]1[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=1)=[O:6]

参加物

実験手順

1M lithium hydroxide (84 ml, 15.4 mmol) was added dropwise to a solution of 6 (3.0 g, 8.53 mmol) in tetrahydrofuran (THF) (100 ml) and the solution stirred at room temperature overnight. Solvent was removed and the aqueous phase washed with chloroform, neutralized to pH 7 with 1M HCl and evaporated to dryness. The solid obtained was suspended in chloroform:methanol (9:1) (100 ml) and stirred for 1 h. The solid was removed by filtration, dried and purified by chromatography (chloroform:methanol, 9:1) to give hapten-I (1.67 g, 58%). NMR 13C(CD3OD) (d, ppm): 172.48, 171.05, 146.92, 146.09, 139.64, 132.69, 130.77, 130.01, 128.91, 127.9, 125.43, 117.55, 115.7, 38.27, 36.64, 30.53 and 21.71. MS: Mass formula (338.1503); Calc. Mass (338.1505).