Production method of amino methyl Bae Nam derivatives and triazolylmethyl Bae Nam derivative

摘要

PURPOSE:To obtain an aminomethylpenam derivative expressed by a specific formula, useful as a starting material for triazolylmethylpenam derivatives to be used as synthetic intermediates for antibiotics, and freed from problems concerning the reaction for obtaining the subject compound, namely, safety, low selectivity and low yield. CONSTITUTION:This compound, an aminomethylpenam derivative, is expressed by formula I (X1 and X2 are each H or a halogen; R1 is H or a carboxylic acid-protecting group; (n) is 0-2), e.g. 2beta-aminomethyl-2alpha-methylpenicillanic diphenylmethyl ester. It is recommended that this derivative of formula I is obtained, for example, by reaction between a compound of formula II and sodium azide to form an azide compound which is, in turn, reduced in the presence of methylene chloride, lead chloride and aluminum powder. The other objective triazolylmethylpenam derivative of formula III is obtained, preferably, by reaction between the compound of formula I and a hydrazone derivative of formula IV (e.g. 2,2'-dichloroacetaldehyde-p-toluenesulfonyl hydrazone) under neutral or basic conditions.