1-[(2S,8S)-8-(bromomethyl)-2-(methoxycarbonyl)-2-methyl-1-oxo-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,2,3,6,7,8-hexahydropyrrolo[3,2-e]indol-4-yl] 4-(tert-butyl) 1,4-piperazinedicarboxylate -Drug Synthesis Database

【结构式】

【分子编号】17754

【品名】1-[(2S,8S)-8-(bromomethyl)-2-(methoxycarbonyl)-2-methyl-1-oxo-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,2,3,6,7,8-hexahydropyrrolo[3,2-e]indol-4-yl] 4-(tert-butyl) 1,4-piperazinedicarboxylate

【CA登记号】

【分子式】C₃₆H₄₂BrN₅O₁₁

【分子量】800.66058

【元素组成】C 54% H 5.29% Br 9.98% N 8.75% O 21.98%

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：(III)

A synthesis of [3H]-KW-2189 has been published: The condensation of duocarmycin B2 (I) with tert-butoxycarbonylpiperazine (II) and 4-nitrophenyl chloroformate by means of triethylamine in dichloromethane gives the expected piperazinecarboxylate (III), which is reduced with NaBH4 in allyl alcohol to yield the hydroxy-derivative (IV). The treatment of (IV) with camphorsulfonic acid (CSA) in hot toluene affords the isomerized compound (V) along with simultaneous deprotection of the piperazine ring. Finally, compound (V) is methylated with tritiated methyl iodide and NaHCO3 in acetone/methanol.

参考文献中间体

合成目标

【1】 Ogasa, T.; Saito, H.; Kinugawa, M.; Nagamura, S.; The synthesis of [H-3]KW-2189, a novel active antitumor antibiotic. J Label Compd Radiopharm 1997, 39, 6, 471.

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)	17752	methyl (2S,8S)-8-(bromomethyl)-4-hydroxy-2-methyl-1-oxo-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,2,3,6,7,8-hexahydropyrrolo[3,2-e]indole-2-carboxylate		C₂₆H₂₆BrN₃O₈	详情	详情
(II)	13225	N-tert-Butoxycarbonyl piperazine; tert-butyl 1-piperazinecarboxylate;tert-butyl piperazine-1-carboxylate	143238-38-4	C₉H₁₈N₂O₂	详情	详情
(III)	17754	1-[(2S,8S)-8-(bromomethyl)-2-(methoxycarbonyl)-2-methyl-1-oxo-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,2,3,6,7,8-hexahydropyrrolo[3,2-e]indol-4-yl] 4-(tert-butyl) 1,4-piperazinedicarboxylate		C₃₆H₄₂BrN₅O₁₁	详情	详情
(IV)	17755	1-[(1R,2S,8S)-8-(bromomethyl)-1-hydroxy-2-(methoxycarbonyl)-2-methyl-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-1,2,3,6,7,8-hexahydropyrrolo[3,2-e]indol-4-yl] 4-(tert-butyl) 1,4-piperazinedicarboxylate		C₃₆H₄₄BrN₅O₁₁	详情	详情
(V)	17756	methyl (8S)-8-(bromomethyl)-2-methyl-4-[(1-piperazinylcarbonyl)oxy]-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-1-carboxylate		C₃₁H₃₄BrN₅O₈	详情	详情

Extended Information