• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】52258

【品名】methyl 4-{[4-(chlorocarbonyl)-2-(methyloxy)-5-nitrophenyl]oxy}butanoate

【CA登记号】

【 分 子 式 】C13H14ClNO7

【 分 子 量 】331.7094

【元素组成】C 47.07% H 4.25% Cl 10.69% N 4.22% O 33.76%

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:(VI)

Vanillic acid (I) was alkylated with ethyl bromobutyrate (II) to afford ether (III). The ester function of (III) was then subjected to saponification, yielding diacid (IV). Nitration of (IV) gave the nitro compound (V). Selective esterification of the aliphatic carboxyl group of (V) was achieved employing p-toluenesulfonic acid in methanol, and the resultant mono-acid was further converted to the corresponding acid chloride (VI) upon treatment with oxalyl chloride. Coupling of acid chloride (VI) with (S)-pyrrolidine-2-carbaldehyde diethyl dithioketal (VII) provided amide (VIII). After the reduction of the nitro group of (VIII) by means of SnCl2, the resultant amino compound (IX) was protected as the N-Fmoc derivative (X). Thioketal deprotection of (X) with concomitant cyclization in the presence of HgCl2 and CaCO3 gave rise to the pyrrolobenzodiazepinone system (XI). The methyl ester of (XI) was then hydrolyzed under acidic conditions to furnish acid (XII).

1 Zhou, Q.; et al.; Design and synthesis of a novel DNA-DNA interstrand adenine-guanine cross-linking agent. J Am Chem Soc 2001, 123, 20, 4865.
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) 17786 4-hydroxy-3-methoxybenzoic acid; Vanillic acid 121-34-6 C8H8O4 详情 详情
(II) 11263 ethyl 4-bromobutanoate; Ethyl 4-bromobutyrate 2969-81-5 C6H11BrO2 详情 详情
(III) 52255 4-{[4-(ethyloxy)-4-oxobutyl]oxy}-3-(methyloxy)benzoic acid C14H18O6 详情 详情
(IV) 52256 4-[(3-carboxypropyl)oxy]-3-(methyloxy)benzoic acid C12H14O6 详情 详情
(V) 52257 4-[(3-carboxypropyl)oxy]-5-(methyloxy)-2-nitrobenzoic acid C12H13NO8 详情 详情
(VI) 52258 methyl 4-{[4-(chlorocarbonyl)-2-(methyloxy)-5-nitrophenyl]oxy}butanoate C13H14ClNO7 详情 详情
(VII) 52259 2-[bis(ethylsulfanyl)methyl]pyrrolidine; ethyl (ethylsulfanyl)(2-pyrrolidinyl)methyl sulfide C9H19NS2 详情 详情
(VIII) 52260 methyl 4-{[4-({2-[bis(ethylsulfanyl)methyl]-1-pyrrolidinyl}carbonyl)-2-(methyloxy)-5-nitrophenyl]oxy}butanoate C22H32N2O7S2 详情 详情
(IX) 52261 methyl 4-{[5-amino-4-({2-[bis(ethylsulfanyl)methyl]-1-pyrrolidinyl}carbonyl)-2-(methyloxy)phenyl]oxy}butanoate C22H34N2O5S2 详情 详情
(X) 52263 methyl 4-{[4-({2-[bis(ethylsulfanyl)methyl]-1-pyrrolidinyl}carbonyl)-5-({[(9H-fluoren-9-ylmethyl)oxy]carbonyl}amino)-2-(methyloxy)phenyl]oxy}butanoate C37H44N2O7S2 详情 详情
(XI) 52262 9H-fluoren-9-ylmethyl 11-hydroxy-7-(methyloxy)-8-{[4-(methyloxy)-4-oxobutyl]oxy}-5-oxo-2,3,11,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-10(5H)-carboxylate C33H34N2O8 详情 详情
(XII) 52264 4-{[10-{[(9H-fluoren-9-ylmethyl)oxy]carbonyl}-11-hydroxy-7-(methyloxy)-5-oxo-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-8-yl]oxy}butanoic acid C32H32N2O8 详情 详情
Extended Information