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    • 3. 发明授权
    • Process for preparing carbapenem compounds
    • 碳青霉烯化合物的制备方法
    • US5204459A
    • 1993-04-20
    • US853069
    • 1992-03-17
    • Shigeo NozoeTomihisa Ohta
    • Shigeo NozoeTomihisa Ohta
    • C07C271/22C07D207/16C07D477/04
    • C07C271/22C07D207/16C07D477/04Y02P20/55
    • Novel amino acid derivatives of the formula ##STR1## wherein R.sup.1 is a protecting group removable under reducing or acid conditions, and R.sup.2 and R.sup.5 are hydrogen or carboxylic protecting groups, are useful as intermediates in preparing stereospecific carbapenam/carbapenem derivatives. R.sup.1 is removed under reducing conditions to form a pyrrolidine derivative, which is further cyclized from the R.sup.5 =H compound to form a .beta.-lactam ring. Stereospecificity at the 6-position is achieved by treatment with lithium diisopropylamide (LDA) and quenching at different temperatures. Compound (I) can be prepared by treating R.sup.1 -protected R.sup.3 -pyrrolidone carboxylic acid R.sup.2 -ester with a lithium enolate of the formula R.sup.4 CHLiCO.sub.2 R.sup.5. The lithium enolate can be formed from R.sup.4 CH.sub.2 CO.sub.2 R.sup.5 by treatment with LDA.
    • 式IMA的新型氨基酸衍生物,其中R 1是在还原或酸性条件下可除去的保护基,R 2和R 5是氢或羧基保护基,可用作制备立体特异性碳青霉烯/碳青霉烯衍生物的中间体。 在还原条件下除去R1以形成吡咯烷衍生物,其进一步从R5 = H化合物环化形成β-内酰胺环。 通过用二异丙基氨基锂(LDA)处理和在不同温度下淬火来实现6位的立体定向性。 化合物(I)可以通过用式R4CHLiCO2R5的烯醇化锂处理R1保护的R3-吡咯烷酮羧酸R2-酯来制备。 烯醇化锂可以通过用LDA处理从R4CH2CO2R5形成。