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1. 发明公开

EP0659742A1 An improved method for the preparation of 2-chloro sulfinyl azetidin-4-one 失效
标题翻译： Verbidityes Verfahren zur Herstellung von 2-Chlorosulfinylazetidin-4-on。
公开(公告)号：EP0659742A1
公开(公告)日：1995-06-28
申请号：EP94309773.3
申请日：1994-12-23
申请人： LUPIN LABORATORIES LIMITED
发明人： Gupta, Niranjan Lal, Lupin Laboratories Limited , Sankaran, Ramanathan, Lupin Laboratories Limited , Sitabkhan, Sakina, Lupin Laboratories Limited
IPC分类号： C07D205/095 , C07D409/12 , C07D501/00
CPC分类号： C07D409/12 , C07D205/095 , C07D501/00 , Y02P20/55
摘要： An improved method for the preparation of 2-chloro sulfinyl azetidin-4-one of the general formula:

wherein R is hydrogen; C₁-C₃ alkyl; halomethyl; cyanomethyl; phenyl, substituted phenyl, phenoxy, benzyloxy or substituted benzyl with the substituent group selected from halo, alkyl, alkoxy, protected hydroxy, nitro, cyano and trifluoromethyl; a group of the formula R₂ -- O -- wherein R₂ is t-butyl, 2,2,2- trichloroethyl, benzyl or substituted benzyl; a group of the formula R₃-(O) n -CH₂ wherein R₃ is phenyl or substi-tuted phenyl with the substituent group selected from halo, alkyl, alkoxy, protected hydroxy, nitro, cyano or trifluoromethyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl or 1,4-cyclohexadienyl, and n is 0 or 1; or a substituted aryl alkyl group of of formula

wherein R₄ has the same meaning as R₃ defined above and W is a protected hydroxy or protected amino group; and R₁ is a carboxylic acid protecting group selected from the group consisting of C₁-C₄ alkyl, 2,2,2-trihalo alkyl, benzyl, substituted benzyl, like p-nitrobenzyl, phenacyl, halo substituted phenacyl and benzhydryl, is disclosed. Such compound is prepared by reacting a penicillin sulfoxide ester of the general formula

wherein R and R₁ have the meanings defined above with an N-chloro halogenating agent in an inert organic solvent. The reaction is carried out in the presence of an acid scavening amount of a phosphate or hydrogen phosphate of an alkali metal, alkaline earth metal, ammonium, quaternary ammonium or mixtures of any thereof. These compounds find application as an intermediate in the production of cefaclor which are powerful anti-bacterial compounds.
摘要翻译：一种制备2-氯亚硫酰基氮杂环丁烷-4-酮的改进方法，其通式为：其中R为氢; C1-C3烷基; 卤; 氰; 苯基，取代的苯基，苯氧基，苄氧基或取代的苄基与选自卤素，烷基，烷氧基，保护的羟基，硝基，氰基和三氟甲基的取代基取代; 式R 2 -O - 的基团，其中R 2是叔丁基，2,2,2-三氯乙基，苄基或取代的苄基; 式R3-（O）n-CH2的基团，其中R3是苯基或具有选自卤素，烷基，烷氧基，保护的羟基，硝基，氰基或三氟甲基的取代基的苯基，2-噻吩基，3-噻吩基，2-呋喃基，3-呋喃基或1,4-环己二烯基，n为0或1; 或具有式CHEM的取代的芳基烷基，其中R 4具有与上述定义的R 3相同的含义，W是受保护的羟基或被保护的氨基; R1是选自C1-C4烷基，2,2,2-三卤代烷基，苄基，取代的苄基，如对硝基苄基，苯甲酰甲基，卤素取代的苯甲酰甲基和二苯甲基的羧酸保护基。通过使惰性有机溶剂中的具有上述定义的R和R 1具有N-氯卤化剂的通式的青霉素亚砜酯反应来制备该化合物。该反应在酸清除量的碱金属，碱土金属，铵，季铵的磷酸盐或磷酸氢盐或其混合物的存在下进行。这些化合物可用作生产头孢克洛的中间体，它们是强大的抗菌化合物。

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