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【结 构 式】

【药物名称】

【化学名称】N-Methyl-2(R)-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-4-oxo-N-[4-(trifluoromethyl)benzyl]azetidine-1-carboxamide

【CA登记号】

【 分 子 式 】C16H17F3N6O2S

【 分 子 量 】414.41209

【开发单位】Bio-Mega (Originator), Boehringer Ingelheim (Originator)

【药理作用】ANTIINFECTIVE THERAPY, Antiviral Drugs, Protease Inhibitors

合成路线1

Silylated 4-oxoazetidine-2-carboxylic acid (I) was converted to the mixed anhydride with isobutyl chloroformate, and then reduced to alcohol (II) with NaBH4. Subsequent Mitsunobu coupling of (II) with mercaptotetrazole (III) provided thioether (IV). Desilylation of (IV) was then achieved by treatment with CsF in MeOH to give (V). Reaction of 4-(trifluoromethyl)benzyl chloride (VI) with methylamine afforded secondary amine (VII). This was reacted with phosgene and diisopropyl ethylamine to produce the carbamoyl chloride (VIII). Finally, condensation of this chloride with azetidinone (V) in the presence of lithium bis(trimethylsilyl)amide furnished the target urea.

1 Yoakim, C.; Ogilvie, W.W.; Cameron, D.R.; Chabot, C.; Grand-Maitre, C.; Guse, I.; Hache, B.; Kawai, S.; Naud, J.; O'Meara, J.A.; Plante, R.; Deziel, R.; Potent beta-lactam inhibitors of human cytomegalovirus protease. Antivir Chem Chemother 1998, 9, 5, 379.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 28418 (2R)-1-[tert-butyl(dimethyl)silyl]-4-oxo-2-azetidinecarboxylic acid C10H19NO3Si 详情 详情
(II) 28419 (4R)-1-[tert-butyl(dimethyl)silyl]-4-(hydroxymethyl)-2-azetidinone C10H21NO2Si 详情 详情
(III) 28420 5-Mercapto-1-methyl-1H-tetrazole; 1-Methyl-1H-1,2,3,4-tetraazol-5-ylhydrosulfide 13183-79-4 C2H4N4S 详情 详情
(IV) 28421 (4R)-1-[tert-butyl(dimethyl)silyl]-4-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-2-azetidinone C12H23N5OSSi 详情 详情
(V) 28422 (4R)-4-[[(1-methyl-1H-1,2,3,4-tetraazol-5-yl)sulfanyl]methyl]-2-azetidinone C6H9N5OS 详情 详情
(VI) 28423 1-(chloromethyl)-4-(trifluoromethyl)benzene 939-99-1 C8H6ClF3 详情 详情
(VII) 28424 N-methyl-N-[4-(trifluoromethyl)benzyl]amine C9H10F3N 详情 详情
(VIII) 28425 1-[[(chlorocarbonyl)(methyl)amino]methyl]-4-(trifluoromethyl)benzene C10H9ClF3NO 详情 详情
Extended Information