54771-63-0Relevant articles and documents
A new approach to the synthesis of cilastatin, an inhibitor of renal dipeptidase
Vinogradov, M. G.,Kaigorodova, L. N.,Chel'tsova-Bebutova, G. V.,Gorshkova, L. S.,Starostin, E. K.,et al.
, p. 167 - 171 (1995)
A convenient preoarative synthesis of cilastatin, an inhibitor of renal dipeptidase used in drugs with the antibiotic imipenem, has been elaborated.The key intermediate in this synthesis is 2-amino-7-chloroheptanoic acid prepared by oxidative cleavage of cycloheptanone followed by bromination of 7-chloroheptanoyl chloride with subsequent amination of the 2-bromo-7-chloroheptanoic acid thus formed.All of the stages of the new synthesis are easily performed, as is the isolation of the intermediate products, and they do not require any organometallic reagents. - Key words: cilastatin, (R)-cysteine, 7-chloroheptanoic acid, 2-amino-7-chloro-2-heptenoic acid, 2,2-dimethylcyclopropanecarbonyl chloride; oxidation, bromination, amination, cyclopropanation.
