PROCESS FOR PRODUCTION OF N-/CHLOR-CARBONIL-OXI/-S-NORBORNENE-2,3-DICARBOXIMIDE

• Main Authors: FORNER,KLAUS,DD, DOELLING,RUDOLF,DD, LOTH,FRITZ,DD, RUPPRICH,CHRISTIAN,DD, BUETTNER,WERNER,DD, DAUTZENBERG,HORST,DD, GRAUL,KARL-HEINZ,DD, HALATSCH,WOLF-RAINER,DD, HENKLEIN,PETER,DD, BECKER,MANFRED,DD
• Format: Patent
• Language: English
• Published: 30.06.1986
• Edition: 4
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; CHEMISTRY; COMPOSITIONS BASED THEREON; HETEROCYCLIC COMPOUNDS; MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVINGCARBON-TO-CARBON UNSATURATED BONDS; MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONSONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS; METALLURGY; ORGANIC CHEMISTRY; ORGANIC MACROMOLECULAR COMPOUNDS; PEPTIDES; THEIR PREPARATION OR CHEMICAL WORKING-UP

(A) N-Chlorocarbonyloxy-5-norbornene -2,3-dicarboximide of formula (I) is new: - (B) Prodn. of protected amino acids or peptides of formula R2NHCOOR R2NHCOOR1 (II), activated carriers of formula (III) and (IV), and carrier-ligand conjugates of formula LCOOQ (V) and L-CO-NR4-Q (VI), is effected by: (a) reacting (I) with an alcohol of formula R1OH and reacting the resulting asymmetric carbonate (VIII) with an amino acid or peptide R2NH2 to form (II): In the formulae R1 = t-Bu, 1-adamantyl, 2-dipherylpropyl (sic), 9-methylfluorenyl, methylsulphonylethyl, benzyl or another gp. normally used in peptide chem.; R2 = an amino acid or peptide residue;. - (b) reacting (I) with an OH-contg. polymer of formula QOH (X) and reacting the resulting activated carrier (IV) with a nucleophilic ligand LH to form a conjugate (V): Q = polymer residue; L = SR3, NHR3 or NR5R6; R3 = H, opt. substd. alkyl, opt. substd. aryl or an amino acid, peptide or protein residue; R5 and R6 = H or opt. substd. alkyl or aryl. - (c) reacting (I) with an insoluble amino-contg. polymer of formula Q-NHR4 (XI) and reacting the resulting activated carrier (IV) with LH to form a conjugate (VI): R4 = H or opt. substd. alkyl or aryl.