1-(4-{4-[4-({[5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methyl}oxy)phenyl]-1-piperazinyl}phenyl)-3-(1-ethyl-2-hydroxypropyl)-1,3-dihydro-2H-imidazol-2-one -Drug Synthesis Database

【结构式】

【分子编号】52651

【品名】1-(4-{4-[4-({[5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methyl}oxy)phenyl]-1-piperazinyl}phenyl)-3-(1-ethyl-2-hydroxypropyl)-1,3-dihydro-2H-imidazol-2-one

【CA登记号】

【分子式】C₃₈H₄₃F₂N₇O₄

【分子量】699.8010064

【元素组成】C 65.22% H 6.19% F 5.43% N 14.01% O 9.15%

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)

The esterification of sodium 4-hydroxybutyrate (I) with 4-nitrobenzyl chloride (II) gives the corresponding ester (III), which is condensed with dibenzyl chlorophosphate (III) in pyridine, yielding the expected phosphoric ester (IV). The cleavage of the 4-nitrobenzyl ester of (IV) with Na2S or Zn/HCl affords the butyric acid derivative (V), which is condensed with SCH-56592 (VI) by means of DMAP and Ts-Cl to provide the corresponding ester (VII). Finally, the benzyl groups of the phosphate moiety of (VII) are cleaved by hydrogenation with H2 or HCOOH over Pd/C in THF, giving rise to the target SCH-59884.

参考文献中间体

合成目标

【1】 Lee, G.M.; et al.; Synthesis of injectable antifungal Sch 59884. Org Process Res Dev 2001, 5, 6, 622.
【2】 Lee, G.M.; et al.; Synthesis of injectable antifungal Sch 59884. (Erratum). Org Process Res Dev 2002, 6, 1, 86.

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)	34856	sodium 4-hydroxybutanoate	502-85-2	C₄H₇NaO₃	详情	详情
(II)	52647	(4-nitrophenyl)methyl 4-hydroxybutanoate		C₁₁H₁₃NO₅	详情	详情
(III)	52648	Chlorophosphoric acid dibenzyl ester; Dibenzylphosphoryl chloride	538-37-4	C₁₄H₁₄ClO₃P	详情	详情
(IV)	52649	(4-nitrophenyl)methyl 4-({bis[(phenylmethyl)oxy]phosphoryl}oxy)butanoate		C₂₅H₂₆NO₈P	详情	详情
(V)	52650	4-({bis[(phenylmethyl)oxy]phosphoryl}oxy)butanoic acid		C₁₈H₂₁O₆P	详情	详情
(VI)	52651	1-(4-{4-[4-({[5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methyl}oxy)phenyl]-1-piperazinyl}phenyl)-3-(1-ethyl-2-hydroxypropyl)-1,3-dihydro-2H-imidazol-2-one		C₃₈H₄₃F₂N₇O₄	详情	详情
(VII)	52652	2-[3-(4-{4-[4-({[5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methyl}oxy)phenyl]-1-piperazinyl}phenyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-1-methylbutyl 4-({bis[(phenylmethyl)oxy]phosphoryl}oxy)butanoate		C₅₆H₆₂F₂N₇O₉P	详情	详情

Extended Information