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【结 构 式】 
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【分子编号】41508 【品名】tert-butyl (3S)-3-[2-(4-[[(tert-butoxycarbonyl)amino]methyl]-2-[[(1R)-1-methyl-2-(4-morpholinyl)-2-oxoethyl]oxy]anilino)-2-oxoethyl]-7-chloro-1,3,4,5-tetrahydrobenzo[cd]indole-2-carboxylate 【CA登记号】 |
【 分 子 式 】C37H47ClN4O8 【 分 子 量 】711.25504 【元素组成】C 62.48% H 6.66% Cl 4.98% N 7.88% O 18% |
合成路线1
该中间体在本合成路线中的序号：(XXIV)Derivative (S)-(XI) is first treated with oxalyl chloride in EtOAc/DMF and coupled with amine (XXIII) in EtOAc in presence of Et3N providing (XXIV). Alternatively (XXIV) can be obtained as follows: reaction of (S)-(XI) with ethyl chloroformate in THF in presence of Et3N. followed by condensation with (XX) in DMF yields phthalimide (XXV). Derivative (XXIV) is then obtained by removal of the phthalate moiety with NH2NH2 and protection with di-t-butyl-dicarbonate. Hydrolysis of (XXIV) with LiOH in THF/MeOH affords carboxylic acid (XXVI) and finally the amine group of (XXVI) is deprotected with HCl in HOAc.
| 【1】 Katayama, S.; Kishimoto, H.; Ae, N.; Nagata, R. (Sumitomo Pharmaceuticals Co., Ltd.); Tricyclic indole-2-carboxylic acid cpd. used as NMDA receptor antagonist. WO 0056711 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (3S)-(XI) | 41497 | 2-[(3S)-7-chloro-2-(methoxycarbonyl)-1,3,4,5-tetrahydrobenzo[cd]indol-3-yl]acetic acid | C15H14ClNO4 | 详情 | 详情 | |
| (XX) | 41506 | 2-(4-amino-3-[[(1R)-1-methyl-2-(4-morpholinyl)-2-oxoethyl]oxy]benzyl)-1H-isoindole-1,3(2H)-dione | C22H23N3O5 | 详情 | 详情 | |
| (XXIII) | 41507 | tert-butyl 4-amino-3-[[(1R)-1-methyl-2-(4-morpholinyl)-2-oxoethyl]oxy]benzylcarbamate | C19H29N3O5 | 详情 | 详情 | |
| (XXIV) | 41508 | tert-butyl (3S)-3-[2-(4-[[(tert-butoxycarbonyl)amino]methyl]-2-[[(1R)-1-methyl-2-(4-morpholinyl)-2-oxoethyl]oxy]anilino)-2-oxoethyl]-7-chloro-1,3,4,5-tetrahydrobenzo[cd]indole-2-carboxylate | C37H47ClN4O8 | 详情 | 详情 | |
| (XXV) | 41509 | methyl (3S)-7-chloro-3-[2-(4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-2-[[(1R)-1-methyl-2-(4-morpholinyl)-2-oxoethyl]oxy]anilino)-2-oxoethyl]-1,3,4,5-tetrahydrobenzo[cd]indole-2-carboxylate | C37H35ClN4O8 | 详情 | 详情 | |
| (XXVI) | 41510 | (2R)-2-[5-[[(tert-butoxycarbonyl)amino]methyl]-2-([2-[(3S)-7-chloro-2-(methoxycarbonyl)-1,3,4,5-tetrahydrobenzo[cd]indol-3-yl]acetyl]amino)phenoxy]propionic acid | C30H34ClN3O8 | 详情 | 详情 |