6-({(11aS)-10-[(allyloxy)carbonyl]-11-hydroxy-7-methoxy-5-oxo-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-8-yl}oxy)hexanoic acid -Drug Synthesis Database

【结构式】

【分子编号】64824

【品名】6-({(11aS)-10-[(allyloxy)carbonyl]-11-hydroxy-7-methoxy-5-oxo-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-8-yl}oxy)hexanoic acid

【CA登记号】

【分子式】C₂₃H₃₀N₂O₈

【分子量】462.49988

【元素组成】C 59.73% H 6.54% N 6.06% O 27.67%

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：(XI)

Cleavage of the trichloroethyl ester of (X) using Zn/HCO2H gives the carboxylic acid (XI). The N-Boc benzindole derivative (XII) is deprotected under acidic conditions to the amine (XIII), which is subsequently coupled with acid (XI) to yield the amide (XIV). Finally, palladium catalyzed cleavage of the N-Alloc group of (XIV) with concomitant dehydration leads to the desired compound.

参考文献中间体

合成目标

【1】 Tercel, M.; Stribbling, S.M.; Sheppard, H.; Siim, B.G.; Wu, K.; Pullen, S.M.; Botting, K.J.; Wilson, W.R.; Denny, W.A.; Unsymmetrical DNA cross-linking agents: Combination of the CBI and PBD pharmacophores. J Med Chem 2003, 46, 11, 2132.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(X)	64823	allyl (11aS)-11-hydroxy-7-methoxy-5-oxo-8-{[6-oxo-6-(2,2,2-trichloroethoxy)hexyl]oxy}-2,3,11,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-10(5H)-carboxylate	C₂₅H₃₁Cl₃N₂O₈	详情	详情
(XI)	64824	6-({(11aS)-10-[(allyloxy)carbonyl]-11-hydroxy-7-methoxy-5-oxo-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-8-yl}oxy)hexanoic acid	C₂₃H₃₀N₂O₈	详情	详情
(XII)	64825	tert-butyl (1S)-1-(chloromethyl)-5-hydroxy-1,2-dihydro-3H-benzo[e]indole-3-carboxylate	C₁₈H₂₀ClNO₃	详情	详情
(XIII)	64826	(1S)-1-(chloromethyl)-2,3-dihydro-1H-benzo[e]indol-5-ol	C₁₃H₁₂ClNO	详情	详情
(XIV)	64827	allyl (11aS)-8-({6-[(1S)-1-(chloromethyl)-5-hydroxy-1,2-dihydro-3H-benzo[e]indol-3-yl]-6-oxohexyl}oxy)-11-hydroxy-7-methoxy-5-oxo-2,3,11,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-10(5H)-carboxylate	C₃₆H₄₀ClN₃O₈	详情	详情

Extended Information