-Drug Synthesis Database

【结构式】

【药物名称】

【化学名称】　

【CA登记号】

【分子式】C₂₇H₃₄N₂O₅S

【分子量】498.64643

【开发单位】

【药理作用】0

合成路线1 合成路线2

合成路线1

The condensation of 5-(benzyloxy)-2,2,4,6,7-pentamethyl-3,4-dihydrobenzofuran-3-ylmethyl methanesulfonate (I) with 2-(methylamino)ethanol (II) by heating at 120 C gives the tertiary amine (III), which is treated with SOCl2 in benzene yielding the chloroethylamino compound (IV). The condensation of (IV) with 4-nitrophenol (V) by means of K2CO3 in hot DMF affords the 4-nitrophenoxy compound (VI), which is reduced with H2 over Pd/C in ethyl acetate to the corresponding 4-aminophenoxy compound (VII). The condensation of (VII) with ethyl acrylate (VIII) by means of NaNO2 and HBr in methanol/water gives the 2-bromopropionic ester (IX), which is cyclized with thiourea (X) by means of NaOAc in refluxing ethanol yielding the thiazolidinedione (XI). Finally, this compound is debenzylated with HCl in hot acetic acid.

参考文献中间体

【1】 Casturi, S.R.; Lohray, V.B.; Kallam, A.R.; Pingali, H.; Ramanujam, R.; Alla, S.R. (Dr. Reddy's Research Foundation); Cpds. having antidiabetic, hypolipidemic, antihypertensive properties, process for their preparation and pharmaceutical compsns. containing them. US 5925656 .

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)	26455	5-(benzyloxy)-2,2,4,6,7-pentamethyl-3-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-2,3-dihydro-1-benzofuran		C₂₄H₃₂O₃S	详情	详情
(II)	13324	2-Methylaminoethanol; 2-(Methylamino)-1-ethanol	109-83-1	C₃H₉NO	详情	详情
(III)	26456	2-[[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl](methyl)amino]-1-ethanol		C₂₄H₃₃NO₃	详情	详情
(IV)	26457	N-[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl]-2-chloro-N-methyl-1-ethanamine		C₂₄H₃₂ClNO₂	详情	详情
(V)	11236	4-Nitrophenol; p-Nitrophenol	100-02-7	C₆H₅NO₃	详情	详情
(VI)	26458	N-[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl]-N-methyl-2-(4-nitrophenoxy)-1-ethanamine		C₃₀H₃₆N₂O₅	详情	详情
(VII)	26459	4-[2-[[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl](methyl)amino]ethoxy]aniline		C₃₀H₃₈N₂O₃	详情	详情
(VIII)	10164	ethyl acrylate	140-88-5	C₅H₈O₂	详情	详情
(IX)	26460	ethyl 3-(4-[2-[[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl](methyl)amino]ethoxy]phenyl)-2-bromopropanoate		C₃₅H₄₄BrNO₅	详情	详情
(X)	10180	Thiourea	62-56-6	CH₄N₂S	详情	详情
(XI)	26461	5-(4-[2-[[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl](methyl)amino]ethoxy]benzyl)-1,3-thiazolidine-2,4-dione		C₃₄H₄₀N₂O₅S	详情	详情

合成路线2

The condensation of the chloromethylamino intermediate (IV) with 5-(4-hydroxybenzyl)thiazolidine-2,4-dione (XII) by means of NaH in in hot DMF gives the previously reported intermediate (XI), which is finally deprotected with HCl in acetic acid as before.

参考文献中间体

【1】 Casturi, S.R.; Lohray, V.B.; Kallam, A.R.; Pingali, H.; Ramanujam, R.; Alla, S.R. (Dr. Reddy's Research Foundation); Cpds. having antidiabetic, hypolipidemic, antihypertensive properties, process for their preparation and pharmaceutical compsns. containing them. US 5925656 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	26457	N-[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl]-2-chloro-N-methyl-1-ethanamine		C₂₄H₃₂ClNO₂	详情	详情
(XI)	26461	5-(4-[2-[[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl](methyl)amino]ethoxy]benzyl)-1,3-thiazolidine-2,4-dione		C₃₄H₄₀N₂O₅S	详情	详情
(XII)	26462	5-(4-hydroxybenzyl)-1,3-thiazolidine-2,4-dione	74772-78-4	C₁₀H₉NO₃S	详情	详情

Extended Information