benzyl (1R,2S,3S)-3-([(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]oxy)-2-(4-fluorophenyl)cyclopentyl(methyl)carbamate -Drug Synthesis Database

【结构式】

【分子编号】40788

【品名】benzyl (1R,2S,3S)-3-([(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]oxy)-2-(4-fluorophenyl)cyclopentyl(methyl)carbamate

【CA登记号】

【分子式】C₃₀H₂₈F₇NO₃

【分子量】583.5460824

【元素组成】C 61.75% H 4.84% F 22.79% N 2.4% O 8.23%

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：(XX)

Addition of benzyl alcohol (C) to isocyanate (XVIII) gave rise to carbamate (XIX), which was further N-alkylated with iodomethane and NaH. Hydrogenolysis of carbamate (XX) over Pd/C produced methyl amine (XXI). This was then converted to the target triazolylmethyl derivative by alkylation with N-formyl-2-chloroacetamidrazone (XXII), followed by thermal cyclization in refluxing xylene.

参考文献中间体

合成目标

【1】 MacCoss, M.; Meurer, L.C.; Finke, P.E.; et al.; Discovery of potent human NK1 antagonists having a cyclopentane-based core structure. 219th ACS Natl Meet (March 26 2000, San Francisco) 2000, Abst MEDI 98.
【2】 Finke, P.E.; Maccoss, M.; Meurer, L.C.; Mills, S.G.; Caldwell, C.G.; Chen, P.; Durette, P.L.; Hale, J.; Holson, E.; Kopka, I.; Robichaud, A. (Merck & Co., Inc.); Cyclopentyl tachykinin receptor antagonists. EP 0858444; WO 9714671 .
【3】 Caldwell, C.G.; Chen, P.; Durette, P.L.; Finke, P.; Hale, J.; Holson, E.; Kopka, I.; Maccoss, M.; Meurer, L.; Mills, S.G.; Robichaud, A. (Merck & Co., Inc.); Cycloalkyl tachykinin receptor antagonists. US 5750549 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XVIII)	40786	(1R,2S,3S)-3-([(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]oxy)-2-(4-fluorophenyl)cyclopentyl isocyanate; 1-((1R)-1-[[(1S,2S,3R)-2-(4-fluorophenyl)-3-isocyanatocyclopentyl]oxy]ethyl)-3,5-bis(trifluoromethyl)benzene		C₂₂H₁₈F₇NO₂	详情	详情
(XIX)	40787	benzyl (1R,2S,3S)-3-([(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]oxy)-2-(4-fluorophenyl)cyclopentylcarbamate		C₂₉H₂₆F₇NO₃	详情	详情
(XX)	40788	benzyl (1R,2S,3S)-3-([(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]oxy)-2-(4-fluorophenyl)cyclopentyl(methyl)carbamate		C₃₀H₂₈F₇NO₃	详情	详情
(XXI)	40789	N-[(1R,2S,3S)-3-([(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]oxy)-2-(4-fluorophenyl)cyclopentyl]-N-methylamine; (1R,2S,3S)-3-([(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]oxy)-2-(4-fluorophenyl)-N-methylcyclopentanamine		C₂₂H₂₂F₇NO	详情	详情
(XXII)	40790	2-chloro-N'-formylethanehydrazonamide		C₃H₆ClN₃O	详情	详情
(C)	18710	Benzyl alcohol; Phenylmethanol	100-51-6	C₇H₈O	详情	详情

Extended Information