(2S)-2-[[4-((2-Chloroethyl)[2-[(methylsulfonyl)oxy]ethyl]amino)benzoyl]amino]pentanedioic acid -Drug Synthesis Database

【结构式】

【分子编号】13679

【品名】(2S)-2-[[4-((2-Chloroethyl)[2-[(methylsulfonyl)oxy]ethyl]amino)benzoyl]amino]pentanedioic acid

【CA登记号】

【分子式】C₁₇H₂₃ClN₂O₈S

【分子量】450.897

【元素组成】C 45.28% H 5.14% Cl 7.86% N 6.21% O 28.39% S 7.11%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(VII)

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).

参考文献中间体

合成目标

【1】 Springer, C.J.; Mann, J.; Bagshawe, K.D.; Haase-Held, M.; Synthesis of an N-mustard prodrug. Tetrahedron 1990, 46, 5377-82.
【2】 Antoniw, P.; Bisset, G.M.F.; Springer, C.J.; Searle, F.; Jarman, M.; Bagshawe, K.D.; Novel prodrugs which are activated to cytotoxic alkylating agents by carboxypeptidase G2. J Med Chem 1990, 33, 2, 677-81.
【3】 Springer, C.J.; CMDA. Drugs Fut 1993, 18, 3, 212.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	18941	p-nitrobenzoyl chloride; 4-nitrobenzoyl chloride	122-04-3	C₇H₄ClNO₃	详情	详情
(II)	13674	di(tert-butyl) (2S)-2-[(4-nitrobenzoyl)amino]pentanedioate		C₂₀H₂₈N₂O₇	详情	详情
(III)	13675	di(tert-butyl) (2S)-2-[(4-aminobenzoyl)amino]pentanedioate		C₂₀H₃₀N₂O₅	详情	详情
(IV)	13676	di(tert-butyl) (2S)-2-([4-[(2-chloroethyl)amino]benzoyl]amino)pentanedioate		C₂₂H₃₃ClN₂O₅	详情	详情
(V)	13677	di(tert-butyl) (2S)-2-([4-[(2-chloroethyl)(2-hydroxyethyl)amino]benzoyl]amino)pentanedioate		C₂₄H₃₇ClN₂O₆	详情	详情
(VI)	13678	di(tert-butyl) (2S)-2-[[4-((2-chloroethyl)[2-[(methylsulfonyl)oxy]ethyl]amino)benzoyl]amino]pentanedioate		C₂₅H₃₉ClN₂O₈S	详情	详情
(VII)	13679	(2S)-2-[[4-((2-Chloroethyl)[2-[(methylsulfonyl)oxy]ethyl]amino)benzoyl]amino]pentanedioic acid		C₁₇H₂₃ClN₂O₈S	详情	详情
(VIII)	13680	4-((2-Chloroethyl)[2-[(methylsulfonyl)oxy]ethyl]amino)benzoic acid		C₁₂H₁₆ClNO₅S	详情	详情

Extended Information