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【结 构 式】

【分子编号】14658

【品名】methyl (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

【CA登记号】

【 分 子 式 】C26H26BrN3O8

【 分 子 量 】588.41186

【元素组成】C 53.07% H 4.45% Br 13.58% N 7.14% O 21.75%

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:(I)

The reaction of 8(S)-(bromomethyl)-4-hydroxy-2-methyl-1-oxo-6-(5,6,7-trimethoxyindol-2-ylcarbonyl)-1,2,3,6,7,8-hexahydrobenzo[1,2-b:4,3-b']dipyrrole-2-carboxylic acid methyl ester (I) with tert-butyl-dimethylsilyl chloride in DMF gives the corresponding O-silyl derivative (II), which is treated with camphorsulfonic acid (CPS) in hot chloroform to afford 8(S)-(bromomethyl)-4-hydroxy-2-methyl-6-(5,6,7-trimethoxyindol-2-ylcarbonyl)-3,6,7,8-tetrahydrobenzo[1,2-b:4,3-b']dipyrrole-1-carboxylic acid methyl ester (III). Finally, this compound is desilylated with tetrabutylammonium fluoride in THF and condensed with N-methylpiperazine (IV) and 4-nitrophenyl chloroformate by means of triethylamine in dichloromethane.

1 Kanda, Y.; Uosaki, Y.; Saito, H.; Sano, H.; Kobayashi, E.; Morimoto, M.; Nagamura, S. (Kyowa Hakko Kogyo Co., Ltd.); DC-88A derivs. EP 0406749; JP 1991128379; US 5070092; US 5187186 .
2 Castaner, J.; Hoshi, A.; KW-2189. Drugs Fut 1993, 18, 12, 1112.
3 Saito, H.; Gomi, K.; Nagamura, S.; Kanda, Y.; Asai, A.; Kobayashi, E.; Synthesis, antitumor activity and DNA alkylation of duocarmycin analogs. Development of KW2189. 203rd ACS Natl Meet (April 5-10, San Francisco) 1992, Abst MEDI 44.
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) 14658 methyl (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) 14659 methyl (8S)-8-(bromomethyl)-4-[[tert-butyl(dimethyl)silyl]oxy]-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 C32H40BrN3O8Si 详情 详情
(III) 14660 methyl (8S)-8-(bromomethyl)-4-[[tert-butyl(dimethyl)silyl]oxy]-2-methyl-6-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-1-carboxylate C32H40BrN3O7Si 详情 详情
(IV) 10061 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine 109-01-3 C5H12N2 详情 详情
Extended Information