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    An Improved Preparation of N-Hydroxysuccinimide

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    moutaz shaldum
    N-Hydroxysuccinimide is an intermediate used in peptide chemistry to prepare various activated esters of acylamino acids (4,5,6,7). The compound has been known for many years (8,9,l0), but has only recently been obtained in moderate amounts by fusion of succinic anhydride either with hydroxylamine (11) o r hydroxylamine hydrochloride, followed by fractional crystallization. A simple alternative to this later procedure exists in the addition of succinic anhydride to a solution of hydroxylamine, then heating in an inert solvent such as toluene o r xylene to form Nhydroxysuccinamic acid, followed by cyclization under forced esterification conditions to afford the desired product. The principal advantage to the modified method described here is the ability to manipulate large quantities without the need for special apparatus and temperature control

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    An Improved Preparation of N-Hydroxysuccinimide

    Uploaded by

    moutaz shaldum
    149 views2 pages
    N-Hydroxysuccinimide is an intermediate used in peptide chemistry to prepare various activated esters of acylamino acids (4,5,6,7). The compound has been known for many years (8,9,l0), but has only recently been obtained in moderate amounts by fusion of succinic anhydride either with hydroxylamine (11) o r hydroxylamine hydrochloride, followed by fractional crystallization. A simple alternative to this later procedure exists in the addition of succinic anhydride to a solution of hydroxylamine, then heating in an inert solvent such as toluene o r xylene to form Nhydroxysuccinamic acid, followed by cyclization under forced esterification conditions to afford the desired product. The principal advantage to the modified method described here is the ability to manipulate large quantities without the need for special apparatus and temperature control

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    An improved preparation of n-hydroxysuccinimide

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    N-Hydroxysuccinimide is an intermediate used in peptide chemistry to prepare various activated esters of acylamino acids (4,5,6,7). The compound has been known for many years (8,9,l0), but has only recently been obtained in moderate amounts by fusion of succinic anhydride either with hydroxylamine (11) o r hydroxylamine hydrochloride, followed by fractional crystallization. A simple alternative to this later procedure exists in the addition of succinic anhydride to a solution of hydroxylamine, then heating in an inert solvent such as toluene o r xylene to form Nhydroxysuccinamic acid, followed by cyclization under forced esterification conditions to afford the desired product. The principal advantage to the modified method described here is the ability to manipulate large quantities without the need for special apparatus and temperature control

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    149 views2 pages

    An Improved Preparation of N-Hydroxysuccinimide

    Uploaded by

    moutaz shaldum
    N-Hydroxysuccinimide is an intermediate used in peptide chemistry to prepare various activated esters of acylamino acids (4,5,6,7). The compound has been known for many years (8,9,l0), but has only recently been obtained in moderate amounts by fusion of succinic anhydride either with hydroxylamine (11) o r hydroxylamine hydrochloride, followed by fractional crystallization. A simple alternative to this later procedure exists in the addition of succinic anhydride to a solution of hydroxylamine, then heating in an inert solvent such as toluene o r xylene to form Nhydroxysuccinamic acid, followed by cyclization under forced esterification conditions to afford the desired product. The principal advantage to the modified method described here is the ability to manipulate large quantities without the need for special apparatus and temperature control

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    Notes Department of Chemistry, Stanford University

    VOl. 3

    Heterocyclic compounds. VI. An improved preparation of n-hydroxysuccinimide


    Kung- sung !ang ", Donald N. #rattesani and #oris !einstein$ Department of Chemistry, Stanford University Stanford, California %&3'(
    )

    *e+eived De+em,er -', )%.( Stanford, California %&3'(

    N-/ydro0ysu++inimide is an intermediate used in peptide +hemistry to prepare various a+tivated esters of a+ylamino a+ids 1&,(,.,23. he +ompound has ,een 4no5n for many years 16,%,l'3, ,ut has only re+ently ,een o,tained in moderate amounts ,y fusion of su++ini+ anhydride either 5ith hydro0ylamine 1))3 o r hydro0ylamine hydro+hloride, follo5ed ,y fra+tional +rystalli7ation. 8 simple alternative to this later pro+edure e0ists in the addition of su++ini+ anhydride to a solution of hydro0ylamine, then heating in an inert solvent su+h as toluene o r 0ylene to form Nhydro0ysu++inami+ a+id, follo5ed ,y +y+li7ation under for+ed esterifi+ation +onditions to afford the desired produ+t. he prin+ipal advantage to the modified method des+ri,ed here is the a,ility to manipulate large 9uantities 5ithout the need for spe+ial apparatus and temperature +ontrol. :;<:*=>:N 8? 1)-3 N-/ ydro0ysu++inimide. 8 freshly prepared solution o f sodium 1..2' g . , '.-%) g.-atom3 in methanol 1)'' ml.3 5as poured into a stirred suspension of finely- ground hydro0ylamine hydro+hloride 1--.- g . , '.-%) mole3 in methanol 1)'' m l , 3 . he mi0ture 5as reflu0ed on a steam ,ath for ) ( minutes, +hilled in an i+e ,ath for )( minutes, and filtered to remove pre+ipitated sodium +hloride. Su++ini+ anhydride 1-%.) g., '.-%) mole3 5as added in small portions over a several-minute period to the stirred hydro0ylamine filtrate, and the resulting li9uid 5as ,oiled for - hours. :0+ess solvent 5as removed ,y distillation, toluene 1or 0ylene3 1)-'' ml.3 5as mi0ed 5ith the vis+ous NOn leave of a,sen+e from the Department of Chemistry, National ai5an University, aipei, ai5an, *epu,li+ of China $Department of Chemistry, Stanford University
    "

    @or the previous paper in this series, seeA #. !einstein and . 8. /ylton, etrahedron, -', )2-( 1)%.&3

    hydro0ysu++inami+ a+id, and reflu0ing 5as +ontinued for another & hours. During this period, a Dean-Star4 trap 5as used to +olle+t a mi0ture of methanol- toluene-5ater 1-'' ml.3. he hot solvent 5as de+anted, and on standing deposited +rude N-hydro0ysu++inimide, m. p. 6..'-%-.'B. he residual solid in the rea+tion flas4 5as e0tra+ted 5ith a +om,ination of toluene mother li9uor and methyl ethyl 4etone 1)'' m l. 3, and on +on+entration and +ooling afforded a se+ond +rop of produ+t. he analyti+al sample 5as re+rystalli7ed from ethyl a+etate to give )..( g. 1&%B).3 of 5hite fla4es, m.p. %2.'-%6.'B, identi+al 5ith authenti+ materialC infrared +m-BA 3''' 1,road3, )22( 1s3. )2'' 1,road3, )&-' 1 s 3 , )--' 1,road3, )'2' 1 s 3 , and .(( 1 ( 3 . 8+4no5ledgment. his investigation 5as supported ,y funds from the National S+ien+e @oundation, grant D#-(62. National Coun+il o f S+ien+e, *epu,li+ of China, is than4ed for the a5ard of a fello5ship for advan+ed study to one of us 1K- . !ang3. *:@:*:NC:S 1)3 @or the previous paper in this series , seeA #. !einstein and )2-( 1)%.&3. . 8. /ylton, etrahedron, -'. he

    1-3 On leave of a,sen+e fr om the Department of Chemistry, National ai5an University, ai5an, *epu,li+ of China. E. 8m. Chem. SOC., 6., )63% 1)%.&3. 133 o 5hom in9uiries +on+erning t hi s paper should ,e dire+ted.

    aipei,

    1&3 Deorge !. 8nderson, Eoan :. Fimmerman, and @ran+is >. Callahan. 1)%.&3. Eournal of the 8meri+an Chemi+al So+iety. doiA)'.)'-)GHa')'.3a'32, 1(3 Deorge !. 8nderson. 1)%.&3. he use of a+tivated esters in peptide synthesis. >eta,olism. doiA)'.)').Gs''-.-'&%(1.&36''---. 1.3 D. !. 8nderson 8+ta Chim. 8+ad. S+i. /ung. )%.( 123 >. ?I5, ?. Kisfaludy 8+ta Chim. 8+ad. S+i. /ung. )%.( 163 D. :rrera Da77. Chim. =tal. -(, == -( )6%( 1%3 8. Eohnson, Neues Euhr,. >ineral. Deol., =, 6% 1)%'23. 1)'3 D. :. 8mes, . @. Drey )%(( E. Chem. So+, .3) 1)%((3. 1))3 *. !egler, @. Dre5e. and K. >ehlhose, U. S. <atent -,6).,))) 1De+em,er )', )%(23. 1)-3 he melting points are un+orre+ted. he =* spe+trum 5as determined on a <er4in - :lmer >odel &-) spe+trophotometer in a pressed potassium ,romide dis4.

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