公开(公告)号：US5578721A

公开(公告)日：1996-11-26

申请号：US273309

申请日：1994-07-11

申请人： Niranjan L. Gupta ,  Ramanathan Sankaran ,  Shibu Varughese ,  Sakina Sitabkhan

发明人： Niranjan L. Gupta ,  Ramanathan Sankaran ,  Shibu Varughese ,  Sakina Sitabkhan

IPC分类号： C07D501/00 ,  C07D501/08 ,  C07D501/22 ,  C07D501/02

CPC分类号： C07D501/00 ,  Y02P20/55

摘要： A process for the manufacture of 3-exomethylene cepham sulfoxide ester of the formula ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.3 alkyl, halomethyl, phenyl, substituted phenyl cyanomethyl, phenoxy, benzyloxy or substituted benzyl with a substituent group such as that selected from halo, alkyl, alkoxy, protected hydroxy, nitro, cyano and trifiuoromethyl, a group of the formula R.sub.2 --0-- wherein R.sub.2 is t-butyl, 2,2,2-trichloro ethyl, benzyl or substituted benzyl; a group of the formula R.sub.3 --[0].sub.n --CH.sub.2, wherein R.sub.3 is phenyl or substituted phenyl with the substituent group selected from halo, alkyl, alkoxy, protected hydroxy, nitro, cyano, or 1,4-cyclohexadienyl, and n is 0 or 1; or a substituted arylalkyl group of formula R.sub.4 --CH where R.sub.4 has the same meaning as R.sub.3 defined above and W is a protected hydroxy or protected amino group; and R.sub.1 is a carboxylic acid protecting group such as that selected from the group consisting of C.sub.1 -C.sub.4 alkyl, 2,2,2-trihalo alkyl, benzyl, substituted benzyl such as para nitrobenzyl, phenacyl, halo substituted phenacyl and benzhydryl is disclosed. Such compound is prepared by reacting a chlorosulfinylazetidinone of the formula ##STR2## wherein R and R.sub.1 have the same meanings as defined above, with a Lewis Acid type Friedel-Crafts catalyst and a sulfur compound in an inert solvent under anhydrous condition. These compounds find application as an intermediate for the preparation of cephalosporin antibiotics.

摘要翻译： 其中R为氢，C 1 -C 3烷基，卤代甲基，苯基，取代的苯基氰基甲基，苯氧基，苄氧基或取代的苄基，其具有如下选择的取代基的制备式（I）的3-异亚甲基头孢烯亚砜酯的方法： 卤素，烷基，烷氧基，保护的羟基，硝基，氰基和三氟甲基，式R2-0-基团，其中R2是叔丁基，2,2,2-三氯乙基，苄基或取代的苄基; 式R 3 - [O] n -CH 2的基团，其中R 3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1,4-环己二烯基的取代基的取代苯基，n是 0或1; 或式R4-CH的取代芳基烷基，其中R4具有与上述定义的R3相同的含义，W是受保护的羟基或被保护的氨基; 并且R 1是羧酸保护基，例如选自C 1 -C 4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。 通过在无水条件下，在惰性溶剂中使路易斯酸型Friedel-Crafts催化剂和硫化合物与式（VII）中R和R 1具有与上述定义相同的式的氯亚磺酰基氮杂环丁酮反应来制备该化合物。 这些化合物可用作制备头孢菌素抗生素的中间体。

公开(公告)号：US5604222A

公开(公告)日：1997-02-18

申请号：US173757

申请日：1993-12-27

申请人： Niranjan L. Gupta ,  Ramanathan Sankaran ,  Sakina Sitabkhan

发明人： Niranjan L. Gupta ,  Ramanathan Sankaran ,  Sakina Sitabkhan

IPC分类号： C07D205/095 ,  C07D409/12 ,  C07D499/04 ,  C07D501/00 ,  C07D501/10 ,  C07D501/14

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 formula: ##STR1## wherein R is: hydrogen; C.sub.1 -C.sub.3 alkyl; halomethyl; cyanomethyl; phenyl; substituted phenyl; phenoxy, benzyloxy- or substituted benzyl; a group of the formula R.sub.2 --O--wherein R.sub.2 is t-butyl, 2,2,2-trichloroethyl, benzyl or substituted benzyl; a group of the formula R.sub.3 --(O).sub.n --CH.sub.2 wherein R.sub.3 is phenyl or substituted phenyl. The 2-chlorosulfinylazetidin-4-one is prepared by reacting a penicillin sulfoxide ester of the general formula ##STR2## wherein R and R.sub.1 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 scavenging amount of a phosphate or hydrogen phosphate of an alkali metal, alkaline earth metal, ammonium, quaternary ammonium or mixtures thereof. These compounds find application as intermediates in the production of cefaclor which are powerful anti-bacterial compounds.

摘要翻译： 用于制备下式的2-氯亚磺酰基氮杂环丁烷-4-酮的改进方法：; 氰甲基 苯基; 取代的苯基; 苯氧基，苄氧基或取代的苄基; 式R2-O-的基团，其中R2是叔丁基，2,2,2-三氯乙基，苄基或取代的苄基; 式R 3 - （O）n -CH 2的基团，其中R 3是苯基或取代的苯基。 2-氯亚磺酰基氮杂环丁烷-4-酮的制备方法是将惰性有机溶剂中通式为“IMAGE”的青霉素亚砜酯，其中R和R 1具有上述定义与N-氯卤化剂反应。 该反应在酸清除量的碱金属，碱土金属，铵，季铵或其混合物的磷酸盐或磷酸氢盐存在下进行。 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。