dibenzyl 2-methoxy-5-[[(2,3,4,5,6-pentafluorophenyl)sulfonyl]amino]phenyl phosphate -Drug Synthesis Database

【结构式】

【分子编号】40541

【品名】dibenzyl 2-methoxy-5-[[(2,3,4,5,6-pentafluorophenyl)sulfonyl]amino]phenyl phosphate

【CA登记号】

【分子式】C₂₇H₂₁F₅NO₇PS

【分子量】629.498058

【元素组成】C 51.52% H 3.36% F 15.09% N 2.23% O 17.79% P 4.92% S 5.09%

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：(V)

Condensation of pentafluorophenyl sulfonyl chloride (I) with 3-hydroxy-4-methoxyaniline (II) in the presence of pyridine afforded sulfonamide (III). Treatment of (III) with N,N-diisopropyl dibenzylphosphoramidite (A) and tetrazole gave phosphite ester (IV), which was subsequently oxidized to phosphate (V) by means of tert-butyl peroxide. Finally, hydrogenolysis of the benzyl phosphate ester groups of (V) in the presence of Pd/C and 1,4-cyclohexadiene furnished the title compound.

参考文献中间体

合成目标

【1】 Flygare, J.; Medina, J.; Shan, B.; Clark, D.; Rosen, T. (Tularik Inc.); Pentafluorobenzenesulfonamides and analogs. EP 0939627; WO 9805315 .
【2】 Rosen, T.; Medina, J.C.; Flygare, J.; Shan, B.; Clark, D. (Tularik Inc.); Pentafluorobenzenesulfonamides and analogs. EP 0896533; JP 2000505459; US 5880151; WO 9730677 .
【3】 Houze, J.B. (Tularik Inc.); Arylsulfonanilide phosphates. WO 9967258 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	40539	N-[bis(phenylmethoxy)phosphanyl]-N-propan-2-ylpropan-2-amine; bis(benzyloxy)phosphino-diisopropyl-amine	108549-23-1	C₂₀H₂₈NO₂P	详情	详情
(I)	20482	2,3,4,5,6-pentafluorobenzenesulfonyl chloride	832-53-1	C₆ClF₅O₂S	详情	详情
(II)	40539	N-[bis(phenylmethoxy)phosphanyl]-N-propan-2-ylpropan-2-amine; bis(benzyloxy)phosphino-diisopropyl-amine	108549-23-1	C₂₀H₂₈NO₂P	详情	详情
(III)	40542	2,3,4,5,6-pentafluoro-N-(3-hydroxy-4-methoxyphenyl)benzenesulfonamide		C₁₃H₈F₅NO₄S	详情	详情
(IV)	40540	dibenzyl 2-methoxy-5-[[(2,3,4,5,6-pentafluorophenyl)sulfonyl]amino]phenyl phosphite		C₂₇H₂₁F₅NO₆PS	详情	详情
(V)	40541	dibenzyl 2-methoxy-5-[[(2,3,4,5,6-pentafluorophenyl)sulfonyl]amino]phenyl phosphate		C₂₇H₂₁F₅NO₇PS	详情	详情

Extended Information