Delft Cleavage

In addition to 7-ADCA, 7-ACA is also a very useful intermediate for the production of other SSCs (for example cefazolin, cefotaxime, ceftriaxone and cefuroxime). Until recently, 7-ACA was produced chemically from cephalosporin C using the phosphorus pentachloride process or the Delft Cleavage 651. As a result of the good experiences with penicillin amidases and the increasing concern about the amount... 

The synthetic challenge centred around the issue that a -lactam ring is more easily hydrolysed than a normal amide. For a selective hydrolysis, special reaction conditions are required, which differentiate between secondary and tertiary amides. Additionally, the carboxy group must be protected before hand. DSM developed a particular process for this, calling it Delft cleavage . Nowadays, the reaction can be carried out in an intrinsically more elegant way with the known penicillin-acylase, which however, in contrast to earlier methods, is now immobilised (Tab. 5.4). [49]... 

Floor, M., Glycol-Cleavage Oxidation of Polysaccharides and Model Compounds Calcium Complexation of Dicarboxy Glucans, Ph.D. thesis, Delft University of Technology, Delft, The Netherlands, 1989. 

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