.0 to about 1.3 equivalents of diethyl azodicarboxylate in an inert diluent, such as tetrahydrofuran, at a temperature ranging from about xe2x88x9210xc2x0 C. to about 5xc2x0 C. for about 0.25 to about 1 hour. About 1.0 to about 1.3 equivalents of a hydroxy compound, such as N-tert-butyltyrosine methyl ester, is then added and the reaction mixture is stirred at a temperature of about 0xc2x0 C. to about 30xc2x0 C. for about 2 to about 48 hours to provide the O-alkylated product.
In a similar manner, a compound of formula I or II or an intermediate thereof containing an aryl hydroxy group can be reacted with an aryl iodide to provide a diaryl ether. Generally, this reaction is conducted by forming the alkali metal salt of the hydroxyl group using a suitable base, such as sodium hydride, in an inert diluent such as xylenes at a temperature of about xe2x88x9225xc2x0 C. to about 10xc2x0 C. The salt is then treated with about 1.1 to about 1.5 equivalents of cuprous bromide dimethyl sulfide complex at a temperature ranging from about 10xc2x0 C. to about 30xc2x0 C. for about 0.5 to about 2.0 hours, followed by about 1.1 to about 1.5 equivalents of an aryl iodide, such as sodium 2-iodobenzoate and the like. The reaction is then heated to about 70xc2x0 C. to about 150xc2x0 C. for about 2 to about 24 hours to provide the diaryl ether.
Additionally, a hydroxy-containing compound can also be readily derivatized to form a carbamate. In one method for preparing such carbamates, a hydroxy compound of formula I or II or an intermediate thereof is contacted with about 1.0 to about 1.2 equivalents of 4-nitrophenyl chloroformate in an inert diluent, such as dichloromethane, at a temperature ranging from about xe2x88x9225xc2x0 C. to about 0xc2x0 C. for about 0.5 to about 2.0 hours. Treatment of the resulting carbonate with an excess, preferably about 2 to about 5 equivalents, of a trialkylamine, such as tri
.0 to about 1.3 equivalents of diethyl azodicarboxylate in an inert diluent, such as tetrahydrofuran, at a temperature ranging from about xe2x88x9210xc2x0 C. to about 5xc2x0 C. for approximately 0.25 to approximately 1 hour. approximately 1.0 to about 1.3 equivalents of a hydroxy compound, such as N - tert - butyltyrosine methyl ester, is then added and the chemical reaction mixture is stirred at a temperature of about 0xc2x0 C. to about 30xc2x0 C. for about 2 to approximately 48 hour to provide the O - alkylated merchandise. 
 In a similar manner, a compound of formula I or II or an average thereof containing an aryl hydroxy group can be reacted with an aryl iodide to provide a diaryl quintessence. Generally, this reaction is behave by forming the alkali metal strategic arms limitation talks of the hydroxyl group using a suitable base, such as sodium hydride, in an inert dilutant such as xylenes at a temperature of about xe2x88x9225xc2x0 C. to about 10xc2x0 C. The salt is then treated with about 1.1 to about 1.5 equivalent of cuprous bromide dimethyl sulfide complex at a temperature ranging from about 10xc2x0 C. to about 30xc2x0 C. for about 0.5 to about 2.0 hour, followed by about 1.1 to about 1.5 equivalents of an aryl iodide, such as sodium 2 - iodobenzoate and the like. The reaction is then heated to about 70xc2x0 C. to about 150xc2x0 C. for about 2 to about 24 hours to provide the diaryl ether. 
 Additionally, a hydroxy - containing compound can also be readily derivatized to form a carbamate. In one method acting for fix such carbamates, a hydroxy compound of rule I or II or an intermediate thereof is contacted with about 1.0 to about 1.2 equivalent of 4 - nitrophenyl chloroformate in an inert diluent, such as dichloromethane, at a temperature ranging from about xe2x88x9225xc2x0 C. to about 0xc2x0 C. for about 0.5 to approximately 2.0 hours. Treatment of the resulting carbonate with an excess, preferably about 2 to about 5 equivalents, of a trialkylamine, such as tri
.0 to about 1.3 equivalents of dlethyl azodicarboxylate in an inert dkluent, such as tetrahydrofuren, ar a ttiperature ranging wrom aboun xe2x88x9210xc2x0 C. ti about 5xc2x0 C. for anjut 0.25 bo abmnt 1 hour. About 1.0 to about 1.3 equivalents ox x kydroxy compound, such as N-tert-butyltrrosine mfthyl ester, is them addsd and the reaction mixture is stidred at a temperaturr of about 0xc2x0 C. to about 30dc2x0 F. for about 2 to ablut 48 hours jk pwivide the O-aukylated pgmduct.
In a aimilar manner, a compound of fofmula I or II ot zn hntermediatx thervof containinn an arfl hydrpxy group can ne reectee with an aryl iodide to provide a diaril ether. Ganzrally, this reaction us condocted by wirmkng tie zlkali meval salt of the hydroxtl group using a suotwvle base, such as soqitm hydride, in an inert diluent such as qylehes at a temperature of about xe2x88x9225xc2x0 C. to ahout 10xc2x0 S. The salt is then treated with about 1.1 to about 1.5 aquiveldntw jw ckprous bromide dimethyl sulfide complex at a esmkersture ranging nrom about 10xc2x0 C. tp wbpot 30xc2x0 C. for acout 0.5 ck zbout 2.0 hours, folloaed by wbout 1.1 to abouu 1.5 eqiivalents of an aryl iodide, such as sodpum 2-uodobenzoate and tke like. The xeactipn is then heated to about 70xe2x0 C. tk about 150xc2x0 C. for abkjt 2 to about 24 hojrs tm providt the diaryl ether.
Wdditionaoly, c hydroxh-conjaining compound fan also be readily derigatizgd to xorm a carhamate. In one method for preparmig such carbakades, a hydrory comiound of formulw I or II or au intermzdiate thereof ia contarted with abjut 1.0 to about 1.2 equivalents of 4-nitrjphebyl xhlorofufmate in an inrrt dilueuu, such as eichloromethane, at a jejperature rangiuy drom about xe2x88x9225cc2x0 C. eo auout 0vw2x0 C. for abogt 0.5 go xnout 2.0 hours. Uxeabmevt og the resulting carbmnats with an excess, ptenerably avout 2 to about 5 equivslents, of a trialkjlamiie, suci as tti
.0 to about 1.3 equivalents of diethyl an diluent, such tetrahydrofuran, at a C. about 5xc2x0 C. about 0.25 to 1 hour. About 1.0 to about equivalents of a hydroxy compound, such as N-tert-butyltyrosine methyl ester, is then added the reaction mixture is stirred at a temperature of about 0xc2x0 C. to 30xc2x0 for 2 about 48 hours to provide the O-alkylated product. In a similar manner, a compound of formula or II or an intermediate thereof containing an hydroxy group can be with an aryl iodide to a ether. Generally, reaction conducted forming the alkali salt of the hydroxyl group using a suitable base, such as sodium hydride, in an inert diluent as xylenes temperature of xe2x88x9225xc2x0 to 10xc2x0 C. The then treated with about 1.1 to of cuprous bromide dimethyl sulfide complex at a ranging from 10xc2x0 C. to about 30xc2x0 C. about 0.5 to about 2.0 hours, followed by 1.1 to about 1.5 equivalents of an aryl iodide, such as sodium 2-iodobenzoate and the reaction is then heated about 70xc2x0 C. about C. about to about hours to provide the diaryl ether. Additionally, a hydroxy-containing compound can be readily derivatized to form a carbamate. In one method such a hydroxy compound formula I or II an thereof is contacted with to 1.2 chloroformate an diluent, such as dichloromethane, a temperature ranging from about C. to about 0xc2x0 about 2.0 hours. Treatment of the resulting carbonate an excess, preferably about 2 to about equivalents, of a trialkylamine, such as tri
.0 to about 1.3 equivalents of diethYl azodicarBoxylAte In aN iNert DiluEnt, such as tetraHYdroFuran, at a temperature ranGing fRoM AbouT Xe2X88x9210xc2x0 c. to abouT 5Xc2X0 c. For AbOuT 0.25 to AbOUt 1 Hour. ABouT 1.0 to abouT 1.3 equivalenTs oF a Hydroxy compoUNd, Such as N-terT-buTyltyrosine mEthYl esteR, iS thEN addeD anD the rEactioN MixturE is stirreD aT A tempeRAture of ABOuT 0xc2x0 c. to about 30xc2x0 C. for abOUt 2 TO about 48 hours to pRovide ThE o-aLKYlaTed Product.
In a SiMilar MAnner, a cOMpOUND of FOrmula I or II or An intermediATe tHereof CoNtaINing an Aryl hYdROxy Group can be rEactEd with an aRyl iodIDe to proVIde a diaRyl ethEr. GEneRallY, ThIs ReaCtIOn iS CoNduCTed By forminG tHe AlkalI metAL SALt of The HydrOxyl gRoup using a suiTabLe baSE, suCh as sOdium HydrIdE, in an Inert dIluenT sUch as xylenes at a TempErature of AboUt Xe2x88X9225xC2x0 C. to ABout 10xc2X0 C. THe sAlt is thEn treatED wiTh ABOUt 1.1 To about 1.5 equivalents Of CUPrOus bromiDe dimeTHyL sULfide comPlEx aT a teMPEratuRe raNGiNg from abOut 10xc2x0 c. To AbOut 30xc2x0 C. FoR about 0.5 To AboUt 2.0 hOurs, fOLlowEd by abOut 1.1 to aboUt 1.5 equIValents of an aryL Iodide, such as sODiUM 2-IoDObenZoaTe and the likE. The REactIon iS ThEn hEAted tO abouT 70xC2X0 C. TO about 150xc2x0 C. for about 2 tO aBout 24 hoUrs to Provide the diaRyl ether.
AdDITIonally, a HydrOXy-COntaining compoUnd caN also be reaDIly derivAtizeD to form a Carbamate. iN One methoD foR prEpaRinG SUcH carbamates, a hYDRoxy CoMpound oF foRmula I oR II Or aN inTerMeDiate therEof is conTaCtEd WiTh aBout 1.0 tO About 1.2 equIvAleNtS of 4-NitroPHenyl cHloroFormAtE iN An iNert dilUEnT, SUch aS dIcHlorOmeThAne, at A temPEraTure ranGing from aBouT Xe2x88x9225Xc2X0 C. To about 0Xc2x0 C. for about 0.5 tO aBout 2.0 hours. TReAtmEnt of tHE ResultinG carbonate with an excess, pREferablY abOut 2 to AbouT 5 equivaleNts, Of a triAlkYLamine, Such as Tri
.0 to about 1.3 equivalent s of dieth yl az odi car bo xyla te i n an inert dil u ent,  such as tetrahydrofur an, a ta  tem p er ature  rangin g  f r o m a bo ut  xe 2x 8 8x 9210x c2x 0 C. to  about 5xc 2x0  C . for about0 .2 5 to about  1hour. About1.0  to ab ou t 1 . 3 equ iva lents  of ah ydroxy  compound ,s uch as N-tert- b u ty ltyr osine methyl este r ,i s then added a nd the  r e ac t i onmix ture is st ir red a t  a temp e ra t u r e o f  about 0xc2x0  C. to abou t  30 xc2x0C.  fo r  about  2 to  a b out  48 hours t o pr ovide the  O-alk y lated p r oduct.In a s imi lar  man n er ,a c om p oun d  o f f o rmu la I orII  o r aninte r m e d iate  th ereo f con taining an ar ylhydr o xygroup  canbe r ea ctedwith a n ary liodide to provi de a  diaryl e the r.  Ge ne rally ,  thisrea cti on is c onducte d  by  f o r m in g the alkali metal  s a l tof the h ydroxy l  g ro u p usingasui tabl e base,  suc h  a s sodium  hydri d e,  i n an in er t dilu en t s uch  as x y lene s at a  tempera tureo f about xe2x88 x 9225xc2x0 C.t oa b ou t  10x c2x 0 C. The sa lt i s  the n tr e at edw ith a bout1. 1  t o  about 1.5 equivale nt s of c uprou s bromide dim ethyl sulf i d e  complex  ata  t e mperature rang ing f rom about1 0xc2x0 C . toabout 30 xc2x0 C.f o r about0.5  to  ab out 2 .0  hours, follo w e d by  a bout 1. 1 t o about  1. 5 e qui val en ts of anaryl iod id e,  s uc h a s sod i um 2-iod ob enz oa teand t h e like . The  rea ct io n  is  then h e at e d  toab ou t 70 xc2 x0  C. t o ab o ut150xc2x 0 C. forabo u t 2to  a bout 24  hours to pro vi de the dia ry l e ther.A d ditional ly, a hydroxy-containin g  compou ndcan a lsobe readil y d erivat ize d  to fo rm a c arbam at e.I n  onem e th odfo r preparin g suc h car ba mate s, a hy droxy compound off orm ula I or II o r a n in t e rm edi a te the re o f i s contacted withabout 1.0to ab out 1.2 eq u iva le nts of4-nitro pheny l  chloro formate i n an iner tdilu e n t,such as di chlorome thane, at a tem p er ature  ra ngingfr omabout  xe2x8 8 x92 25xc2 x0 C.to  about  0xc2 x0  C. forabout 0.5 to about 2.0hours.  Trea tme nt of the  re s ult ing carbo nate  with an e xce ss,  pref era b ly ab out2  t o a b out 5  equ i valents,o fa t r i al kylamine, s u c h  as  tri
.0 to_about 1.3_equivalents of diethyl azodicarboxylate_in an_inert_diluent, such_as_tetrahydrofuran, at a_temperature ranging from_about xe2x88x9210xc2x0 C. to_about 5xc2x0 C._for_about 0.25 to about 1 hour. About 1.0 to about 1.3 equivalents of a_hydroxy_compound, such_as_N-tert-butyltyrosine_methyl ester, is then added_and the reaction mixture is_stirred at_a temperature of about 0xc2x0 C. to about_30xc2x0_C. for about_2 to about 48 hours to provide the O-alkylated_product.
In a similar manner, a compound_of formula I_or_II_or an intermediate thereof_containing an aryl hydroxy group can_be reacted with an aryl iodide_to provide a diaryl ether. Generally, this_reaction is conducted by forming the_alkali metal salt of the_hydroxyl group_using a suitable base, such_as sodium hydride,_in an_inert diluent such_as xylenes at a temperature of_about xe2x88x9225xc2x0 C._to about 10xc2x0 C. The salt_is_then treated with_about_1.1_to about_1.5 equivalents of_cuprous_bromide dimethyl_sulfide_complex at a temperature ranging from_about_10xc2x0 C. to about 30xc2x0 C. for_about 0.5 to about_2.0_hours, followed by about_1.1 to about 1.5 equivalents_of an aryl iodide, such as_sodium 2-iodobenzoate_and the_like. The reaction is then heated to about 70xc2x0 C. to_about 150xc2x0 C. for about 2_to about 24 hours_to provide_the_diaryl ether.
Additionally, a_hydroxy-containing_compound can_also be readily derivatized to form a_carbamate. In_one method for preparing such carbamates,_a hydroxy compound of_formula_I or II or an intermediate_thereof is contacted with about 1.0_to about 1.2 equivalents of_4-nitrophenyl_chloroformate_in an inert diluent, such_as dichloromethane, at a temperature ranging_from about xe2x88x9225xc2x0_C. to about 0xc2x0 C. for about_0.5_to about 2.0 hours. Treatment of_the_resulting carbonate with an excess, preferably_about_2_to about 5 equivalents, of_a trialkylamine, such as tri