4-Vinylbenzenesulfonyl chloride; p-Styrenesulfonyl chloride; p-Vinylbenzenesulfonyl chloride; 4-Styrenesulfonyl chloride -Drug Synthesis Database

【结构式】

【分子编号】55434

【品名】4-Vinylbenzenesulfonyl chloride; p-Styrenesulfonyl chloride; p-Vinylbenzenesulfonyl chloride; 4-Styrenesulfonyl chloride

【CA登记号】2633-67-2

【分子式】C₈H₇ClO₂S

【分子量】202.66108

【元素组成】C 47.41% H 3.48% Cl 17.49% O 15.79% S 15.82%

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：(II)

The sulfonation of D-tryptophan tert-butyl ester (I) with 4-vinylphenylsulfonyl chloride (II) and NMM in dichloromethane gives N2-(4-vinylphenylsulfonyl)-D-tryptophan tert-butyl ester (III), which is treated with ozone in dichloromethane to yield the benzaldehyde (IV). The condensation of (IV) with phenylsulfonyl hydrazide (V) in ethanol/THF affords the phenylsulfonyl hydrazone (VI), which is cyclized with phenyldiazonium chloride (VII) (aniline, NaNO2 and aq. HCl) in pyridine to provide the tetrazole derivative (VIII). Finally, the tert-butyl ester group of (VIII) is hydrolyzed with THF in dichloromethane to furnish the target D-tryptophan derivative.

参考文献中间体

合成目标

【1】 Watanabe, F.; Tsuzuki, H.; Ohtani, M. (Shionogi & Co. Ltd.); Sulfonated amino acid derivs. and metalloproteinase inhibitors containing the same. EP 0950656; JP 2001316254; US 6207698; US 6235768; US 6441021; WO 9727174 .
【2】 Watanabe, F.; Kurihara, H.; Tamura, Y.; Sinosaki, T. (Shionogi & Co. Ltd.); Therapeutic or prophylactic agent for glomerulopathy. EP 1029541; US 6423729; WO 9904780 .

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)	55433	tert-butyl (2R)-2-amino-3-(1H-indol-3-yl)propanoate		C₁₅H₂₀N₂O₂	详情	详情
(II)	55434	4-Vinylbenzenesulfonyl chloride; p-Styrenesulfonyl chloride; p-Vinylbenzenesulfonyl chloride; 4-Styrenesulfonyl chloride	2633-67-2	C₈H₇ClO₂S	详情	详情
(III)	55435	tert-butyl (2R)-3-(1H-indol-3-yl)-2-{[(4-vinylphenyl)sulfonyl]amino}propanoate		C₂₃H₂₆N₂O₄S	详情	详情
(IV)	55436	tert-butyl (2R)-2-{[(4-formylphenyl)sulfonyl]amino}-3-(1H-indol-3-yl)propanoate		C₂₂H₂₄N₂O₅S	详情	详情
(V)	55437	Benzenesulfonic acid hydrazide; Benzenesulfonyl hydrazide	80-17-1	C₆H₈N₂O₂S	详情	详情
(VI)	55438	tert-butyl (2R)-3-(1H-indol-3-yl)-2-{[(4-{[(E)-2-(phenylsulfonyl)hydrazono]methyl}phenyl)sulfonyl]amino}propanoate		C₂₈H₃₀N₄O₆S₂	详情	详情
(VII)	25897	benzenediazonium chloride		C₆H₅ClN₂	详情	详情
(VIII)	55439	tert-butyl (2R)-3-(1H-indol-3-yl)-2-({[4-(2-phenyl-2H-1,2,3,4-tetraazol-5-yl)phenyl]sulfonyl}amino)propanoate		C₂₈H₂₈N₆O₄S	详情	详情

Extended Information