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CAPLUS COPYRIGHT 2013 ACS
||Method for the chemoselective preparation of hydrazides by acylation of a slurry of hydrazine in an inert solvent with an acid chloride at low temperature and its use in the preparation of 3-mercapto-3-methylbutanoic acid hydrazide
||Chiarello, George A.; Sahli, Ayman
||Wyeth, John, and Brother Ltd., USA
||PCT Int. Appl., 49pp. CODEN: PIXXD2
A method is disclosed for prepg. hydrazides from hydrazine and an acyl chloride by prepg. a stirred and substantially uniform slurry of hydrazine and an inert solvent at low temp. and then adding an acyl chloride continuously to said slurry; the modified method decreases the formation of the bis-hydrazide product present in the desired hydrazide. The method is applied to the prepn. of 4-MeOC6H4CH2SCMe2CH2CONHNH2 (I) from the acid chloride 4-MeOC6H4CH2SCMe2CH2COCl (prepd. in two steps from 3,3-dimethylacrylic acid and 4-methoxybenzylthiol); I is converted to the thiol-contg. hydrazide HSCMe2CH2CONHNH2 (Cl-332258), used as a linker in the prepn. of immunoconjugates of monoclonal antibodies with calicheamicins. The effects of temp., mixing speed, and reactor on the prepn. of I are detd.
Please note: Abstracts and Titles for patent records in CAplus are routinely enhanced to better describe the claimed invention. The title of the U.S. granted patent is Processes for making hydrazides.
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