(E)-3-methoxy-2-methyl-2-propenal -Drug Synthesis Database

【结构式】

【分子编号】31585

【品名】(E)-3-methoxy-2-methyl-2-propenal

【CA登记号】

【分子式】C₅H₈O₂

【分子量】100.11732

【元素组成】C 59.98% H 8.05% O 31.96%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(XXI)

The reaction of 2-methylpropane-1,3-dial (XX) first with methanesulfonyl chloride and then with NaOMe gives 3-methoxy-2-methyl-2-propenal (XXI), which is cyclized with 1-(tert-butyldimethylsilyloxy)-2-butanone (XXII) in basic medium to yield the dihydropyridine (XXIII). Finally, this compound is dehydrogenated with DDQ and desilylated to afford the target intermediate 4-methoxy-3,5-dimethylpyridine-2-methanol (VI).

参考文献中间体

合成目标

【1】 Bekhazi, M.; Zoghbi, M. (PDi-Research Laboratories, Inc. ); Synthesis of omeprazole-type pyridine derivs. and intermediates thereof. WO 9729103 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(VI)	18785	(4-methoxy-3,5-dimethyl-2-pyridinyl)methanol	C₉H₁₃NO₂	详情	详情
(XX)	31584	2-methylmalonaldehyde	C₄H₆O₂	详情	详情
(XXI)	31585	(E)-3-methoxy-2-methyl-2-propenal	C₅H₈O₂	详情	详情
(XXII)	31586	1-[[tert-butyl(dimethyl)silyl]oxy]-2-butanone	C₁₀H₂₂O₂Si	详情	详情
(XXIII)	31587	2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-4-methoxy-3,5-dimethyl-1,4-dihydropyridine; tert-butyl(dimethyl)silyl (4-methoxy-3,5-dimethyl-1,4-dihydro-2-pyridinyl)methyl ether	C₁₅H₂₉NO₂Si	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XXI)

The reaction of 1-hydroxy-2-butanone (XXIV) with tosyl chloride gives the tosylate (XXV), which is condensed with 5-methoxy-1H-benzimidazole-2-thiol (VIII) yielding 5-methoxy-2-(2-oxobutylsulfanyl)-1H-benzimidazole (XXVI). The reaction of (XXVI) with 3-methoxy-2-methyl-2-propenal (XXI) in basic medium affords the 5-oxohexanal derivative (XXVII), which is cyclized by means of NH4OAc and NH3 to give the dihydropyridine (XXVIII). Finally, this compound is dehydrogenated and oxidized to the target sulfinyl derivative.

参考文献中间体

合成目标

【1】 Bekhazi, M.; Zoghbi, M. (PDi-Research Laboratories, Inc. ); Synthesis of omeprazole-type pyridine derivs. and intermediates thereof. WO 9729103 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VIII)	29924	5-Methoxy-1H-benzimidazol-2-ylhydrosulfide; 2-Mercapto-5-methoxybenzimidazole; 5-Methoxy-1H-benzimidazole-2-thiol; 5-Methoxy-2-mercaptbenzimidazole; 5-Methoxy-2-Benzimidazolethiol	37052-78-1	C₈H₈N₂OS	详情	详情
(XXI)	31585	(E)-3-methoxy-2-methyl-2-propenal		C₅H₈O₂	详情	详情
(XXIV)	31588	1-hydroxy-2-butanone	5077-67-8	C₄H₈O₂	详情	详情
(XXV)	31589	2-oxobutyl 4-methylbenzenesulfonate		C₁₁H₁₄O₄S	详情	详情
(XXVI)	31590	1-[(5-methoxy-1H-benzimidazol-2-yl)sulfanyl]-2-butanone		C₁₂H₁₄N₂O₂S	详情	详情
(XXVII)	31591	3-methoxy-6-[(5-methoxy-1H-benzimidazol-2-yl)sulfanyl]-2,4-dimethyl-5-oxohexanal		C₁₇H₂₂N₂O₄S	详情	详情
(XXVIII)	31592	2-[[(5-methoxy-1H-benzimidazol-2-yl)sulfanyl]methyl]-3,5-dimethyl-1,4-dihydro-4-pyridinyl methyl ether; 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-1,4-dihydro-2-pyridinyl)methyl]sulfanyl]-1H-benzimidazole		C₁₇H₂₁N₃O₂S	详情	详情

合成路线3

该中间体在本合成路线中的序号：(XXI)

The reaction of tosylate (XXV) with potassium ethylxanthate (XXIX) gives the adduct (XXX), which is cyclized with 3-methoxy-2-methyl-2-propenal (XXI) by means of t-BuOK, NH4Cl and NH3 in THF yielding the dihydropyridine (XXXI). The oxidation of (XXXI) with MCPBA in chloroform affords the pyridine (XXXII), with simultaneous formation of the sulfinyl group. Finally, this compound is cyclized with 4-methoxyphenylene-1,2-diamine (XXXIII) by means of TFA in refluxing toluene.

参考文献中间体

合成目标

【1】 Bekhazi, M.; Zoghbi, M. (PDi-Research Laboratories, Inc. ); Synthesis of omeprazole-type pyridine derivs. and intermediates thereof. WO 9729103 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XXI)	31585	(E)-3-methoxy-2-methyl-2-propenal		C₅H₈O₂	详情	详情
(XXV)	31589	2-oxobutyl 4-methylbenzenesulfonate		C₁₁H₁₄O₄S	详情	详情
(XXIX)	29923	o-Ethylxanthic acid potassium salt; Potassium ethyl xanthogenate; potassium 1-(carbodithioatooxy)ethane	140-89-6	C₃H₅KOS₂	详情	详情
(XXX)	31593	O-ethyl S-(2-oxobutyl) carbonodithioate		C₇H₁₂O₂S₂	详情	详情
(XXXI)	31594	S-[(4-methoxy-3,5-dimethyl-1,4-dihydro-2-pyridinyl)methyl] O-methyl carbonodithioate		C₁₁H₁₇NO₂S₂	详情	详情
(XXXII)	31595	O-methyl [(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl](oxo)-lambda(4)-sulfanecarbothioate		C₁₁H₁₅NO₃S₂	详情	详情
(XXXIII)	29922	2-amino-4-methoxyphenylamine; 4-methoxy-1,2-benzenediamine	102-51-2	C₇H₁₀N₂O	详情	详情

Extended Information