合成路线:The synthesis of CMDA (VII) was accomplished using a modified version of the published procedures:The di-tert-butyl 4-nitrobenzoyl-L-glutamate (II) was reduced to di-tert-butyl 4-aminobenzoyl-L-glutamate (III) using transfer hydrogenation.The reductive amination of (III) with chloroethanal yielded the monofunctional di-tert-butyl 4-[(2-chloroethyl)amino]benzoyl-L-glutamate (IV),which was N-alkylated with ethylene oxide to give di-tert-butyl 4-[(2-chloroethyl)(2-hydroxyethyl)amino]benzoyl-L-glutamate (V).Reaction of (V) with methanesulfonyl chloride at 5 C yielded di-tert-butyl 4-[(2-chloroethyl)[2-(mesyloxy)ethyl]amino]benzoyl-L-glutamate (VI).Treatment of (VI) with formic acid followed by lyophilization gave the diacid,4-[(2-chloroethyl)[2-(mesyloxy)ethyl]amino]benzoyl-L-glutamic acid (VII).
参考文献标题:Novel prodrugs which are activated to cytotoxic alkylating agents by carboxypeptidase G2
文献作者:Springer,C.J.; Antoniw,P.; Bagshawe,K.D.; Searle,F.; Bisset,G.M.F.; Jarman,M.
参考来源:J Med Chem 1990,33(2),677-81
合成路线:The synthesis of CMDA (VII) was accomplished using a modified version of the published procedures:The di-tert-butyl 4-nitrobenzoyl-L-glutamate (II) was reduced to di-tert-butyl 4-aminobenzoyl-L-glutamate (III) using transfer hydrogenation.The reductive amination of (III) with chloroethanal yielded the monofunctional di-tert-butyl 4-[(2-chloroethyl)amino]benzoyl-L-glutamate (IV),which was N-alkylated with ethylene oxide to give di-tert-butyl 4-[(2-chloroethyl)(2-hydroxyethyl)amino]benzoyl-L-glutamate (V).Reaction of (V) with methanesulfonyl chloride at 5 C yielded di-tert-butyl 4-[(2-chloroethyl)[2-(mesyloxy)ethyl]amino]benzoyl-L-glutamate (VI).Treatment of (VI) with formic acid followed by lyophilization gave the diacid,4-[(2-chloroethyl)[2-(mesyloxy)ethyl]amino]benzoyl-L-glutamic acid (VII).
参考文献标题:Synthesis of an N-mustard prodrug
文献作者:Springer,C.J.; Mann,J.; Bagshawe,K.D.; Haase-Held,M.
参考来源:Tetrahedron 1990,465377-82
产品链接: CAS No. 122665-73-0››