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lkAyltaio ofn2 -hydoryxpyriined(HAS B applcitioa) nWithso f tlecetorhpies, lN-laklytaios cann be erfproedm (elbwoS chmee). TheM istunbour eacitnos moeitem lsaesd t oOa-kllatiyon xeluscveil,y ropablyb uedt o het hrd chaaractre f tho eitenmreditea.Rh doim uarcenb (hared) ocpmlx alseo peferentialrylal klatey teh O atom.1.eq 5acrloie 120 nC,0 C 6H, 262 hNH O95 2%qe2 bromo-etanohl 1.5qeK2C O, 3570C, a etocn, e1h 2NH O 5% N O O5 H12.eq5P ChHC22OH 1H.eq PPh3,5 .15q DEAe D02 C0,TH FN H 88O%1.e3qN 2CHC2EO 2% th2RO(CC2F)4 34 00, CC2HlC 2 HN 8O7 N%O CO E2 tN PO NhO OAlkylaiot ofnamide sa dnlacta s m-aNlkyltiaos aren gnerelal coyductedn ndur baeis condicions twhreesa -Oaklyatiolsn aer fotn eprfeormdew ih trtilkayoxolnum ialts,sdi alyk slulatef, sr alkoyl haldeiss/lvirealstsw ithuo taddtiin oo fabsse. elBo wchSmee shws exoampel sf toe shelecive tN -nd a aOklyaltin oof altacm.sPhN HO+ Br0 B1

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N5 OOB rN HhP1qe ABFg,4M 2eC ONtE 903%ON PhHNON N11. eq5 t3EOBF4, C2Cl2 H020 C,2 1h9%3N

O NNOrg L.tt.e2 000,2,164 1-1634; .J Or. gChem. 9912, 75,5708-7125;eTtahredron eLtt 19.94, 35,2189-822.2

J .A. Chmm. Seco.1 71, 99,3 1551-155;5J .mA.C eh.m Soc 2002.,124, 6573-683;5 TtreahdreonL et.t1 899 29,, 571-6674;5 rg.OP oc. rRs.eD e. 20v01 5,, 55-750.

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emAde Bind oFrmotioa2n.1C holrformaot (ClCeORO):OB n OO OOC CHH3 ClOCO2HC,5T AE, THF,t eh NHn (3)g 20 oC -o rtt.6 5% Bn O OO

iJpenn gLiIntrodctioun: Aimed obdn pla ay mjor raloein th e elaorabtion nd acmposoitinoof ioboligal scystes,m na idtr epersnes tteh amin hcmecali bod tnaht ilknam noia cd biiudlni glboksctoge hetr o tormf proteins A.mde biond si no otnl yimlite tdobio lgiocla ystessmb t ulso indaede rpeent in a sugehar rayo molfecluse, icludnni gamjo mrrkated ephrmaacetuciladr ugs Par. It Co.nendasiton fo Amin ewith Aic 1d .Diertc Cndoneasion tfo mAie wnih AcitOrgd P.er.p rPoc In..t2000, 32 ()1,848-HOC82COHO+H PCh2HH2N9 0C Oo OCHH2C NCHH2PhCON2HC H3Snth. Comymu.,n 200, 344,519170

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O. 3Coulipgn Uisn Cargodiibmdi MeechnaisR m OO R1N C NhPRR1 O NC O NH R2A Pa th Rb O1 RNO N PHth aaSytnheiss19 89, 7457-47 2O SN OCl2HN R 2

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2 OR

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TDertaehron Ledt. t199,53 6, 175-17181

Nomraly, thle ixedma nyhrddieo f (oB

c)O 2i ssuedi then prpaeration o faimde rof pmirmry amanie.s

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