Hydrazinolysis study of phthalimido- and phthalisoimido-penicillin amide derivatives

Abstract

New phthalimido-penicillin amide (6-PhtPABn) and phthalisoimido-penicillin amide (6-isoPhtPABn) were prepared and the susceptibility of their different carbonyl functions toward hydrazine derivatives investigated in order to establish the feasibility of dephthaloylation within penicillin class compounds. Hydrazinolysis of phthalimido-penicillin amide (6-PhtPABn) resulted in dephthaloylation and β-lactam ring opening into thiazolidine derivatives, while in the case of phthalisoimido-penicillin amide (6-isoPhtPABn), the desired amino-penicillin amide (6-APABn) was isolated in low yield.

An Improved Scalable Route to Pure Dronedarone Hydrochloride

“…In an attempt to overcome these difficulties, we protected the amino group of benzofuran 10 as its corresponding phthalimido derivative which would be stable for a wide verity of reaction conditions. 6,7 Moreover, deprotection of the phthalimido group can be achieved under very mild condition using MeNH 2.…”

“…As mentioned in scheme , the Friedel–Crafts acylation on sulfonamide 11 with acid chloride 9 was low yielding and accompanied by several impurities. In an attempt to overcome these difficulties, we protected the amino group of benzofuran 10 as its corresponding phthalimido derivative which would be stable for a wide verity of reaction conditions. , Moreover, deprotection of the phthalimido group can be achieved under very mild condition using MeNH 2. With this intention, amino benzofuran 10 was treated with phthalic anhydride in the presence of triethylamine to provide the phthalimido derivative 12 .…”