Methanethiol → Ethyl 2-butyl-1-[[2'-(methoxycarbonyl)-(1,1'-biphenyl)-4-yl]-methyl]-4-(methylthio)-1H-imidazole-5-carboxylate

반응식

[CH2:1]([C:5]1[NH:6][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:8]([S:10][CH3:11])[N:9]=1)[CH2:2][CH2:3][CH3:4].CS.Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[C:28]([C:33]([O:35][CH3:36])=[O:34])=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:23][CH:22]=1>>[CH2:1]([C:5]1[N:6]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]([O:35][CH3:36])=[O:34])=[CH:23][CH:22]=2)[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:8]([S:10][CH3:11])[N:9]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

반응물 3

HCID 878Methanethiol

HCID 9859628Ethyl 2-butyl-5-methylsulfanyl-3H-imidazole-4-carboxylate

HCID 11012181Methyl 4'-(bromomethyl)biphenyl-2-carboxylate

생성물 1

HCID 21479063Ethyl 2-butyl-1-[[2'-(methoxycarbonyl)-(1,1'-biphenyl)-4-yl]-methyl]-4-(methylthio)-1H-imidazole-5-carboxylate수율 69.3%

실험 절차

The operation is carried out as in Example 5, starting with 0.6 g of ethyl 2-butyl-4-(methylthio)-1H-imidazole-5-carboxylate (prepared as indicated in Stages C and D of Preparation 1, replacing the ethanethiol with methanethiol), using 907 mg of methyl 4'-(bromomethyl)-(1,1'-biphenyl)-2 -carboxylate. After chromatography on silica (eluant: methylene chloride--ethyl acetate (97-3)), 0.8 g of the desired product is obtained.