Convenient one-pot esterification of N-protected aminoacids via isopropenyl chloroformate activation

TetrahedronLetters,Vol.28,No.lS,pp1661-1664,1987oo40-4039/87$3.00+.OOPrintedinGreatBritainPergamonJournalsLtd.CONVENIENTONE-POTESTEWFICATIONOFN-PROTECTEDAMINOACIDSvfeISOPAOPENYLCHLOROFOlWATEACTIVATK)N.P.Jouin*,8.Castro,C.Zeggaf,A.PantaioniCCIPE.ruedelaCardonilie,34094Montpeiiiercedex.J.P.Senet,S.Lecoiier,G.Sennyey.SNPE.CentrederecherchesduBouchet.91710VertlePetit.Summary:Act/vat/onofN-protectedamlnoacidsbylsopropenylchloroformateleadstoestersofprimary,secondaryandtertiaryalcoholswlth4-dlmethylamlno-pyrldineascatalyst.EstersofN-protecteda-aminoacidsarecommonlypreparedfromaikyihalides.iAlthoughnumerousmethodsareavailablefortheactivationofN-protectedaminoacids.2onlyfewsimpleprocessesallowesterificationofaminoacidsfromalcoholundermildconditions.)*4inthecourseofourinvestlgationonisopropenyichloroformate(IPCF)2breactivity.wenowreportanefficientone-potesterificationofN-protectedaminoacidswithalcohols.byusingIPCFfortheacidactivation.isopropenyichiororoformateLbhasalreadybeenusedfortheaminoaci