Synthesis of 1-(allyloxycarbonyl)-methyl-3-(hydroxyethyl)-4-beta

Details Synthesis of 1-(allyloxycarbonyl)-methyl-3-(hydroxyethyl)-4-beta Synthesis of 1-(allyloxycarbonyl)-methyl-3-(hydroxyethyl)-4-beta

1986-07-21

1988-08-30

Berch, Mark L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

540304, 540358, 540354, C07D20508, C07D51304, C07D40312, C07F 718

Patent

active

047678534

ABSTRACT:
A multi-step stereospecific process for preparing (3S,4R,5R)-1-(allyloxycarbonyl)-methyl-3-(1-hydroxyethyl)-4-beta-naphthoxy thiocarbonylthio-2-azetidinones, stereoisomers thereof or hydroxy protected analogs thereof from anhydropenicillin. The azetidinones are intermediates useful for producing penems which are a known group of antibacterial compounds. The process involves protecting the hydroxy group of anhydropenicillin with a readily removable hydroxy protecting group, then converting the resulting compound by ozonolysis followed by reaction with a trialklyl phosphite, then hydrolysis to remove the methylidene group at the 2-position of anhydropenicillin. The resulting compound is converted to the unprotected 4-beta-naphthoxy thiocarbonylthio derivative by reaction with allyl alcohol and HCl followed by reaction with O-2-napththalenylcarbonochloridothioate, or to the protected compound by reaction with silver imidazolate and allyl alcohol followed by reaction with O-2-naphthalenylcarbonochloridothioate.

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