methyl 3-hydroxy-4-(hydroxymethyl)benzoate -Drug Synthesis Database

【结构式】

【分子编号】36153

【品名】methyl 3-hydroxy-4-(hydroxymethyl)benzoate

【CA登记号】

【分子式】C₉H₁₀O₄

【分子量】182.176

【元素组成】C 59.34% H 5.53% O 35.13%

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 partial reduction of dimethyl hydroxyterephthalate (I) with NaBH4 in refluxing methanol gives methyl-3-hydroxy-4-(hydroxymethyl)benzoate (II), which by reaction with 2,2-dimethoxypropane (III) by means of p-toluenesulfonic acid in benzene is converted into the benzo-1,3-dioxane (IV). The reduction of (IV) with sodium dihydro-bis(2-methoxyethoxy)aluminate (V) affords the protected benzyl alcohol (VI), which is oxidized with CrO3 to the benzaldehyde (VII). The reaction of (VII) with NaCN and ammonia in methanol yields the aminonitrile (VIII), which is finally hydrolyzed with Ba(OH)2 and afterwards with H2SO4.

参考文献中间体

合成目标

【1】 Yoshizawa, J.; Ushijima, R.; Umezawa, H.; Takeuchi, T.; Morishima, H.; Synthesis of forphenicinol and forphenicine. J Antibiot 1982, 35, 11, 1500-06.
【2】 Aoyagi, T.; Ishizuka, M.; Matsumoto, I,. Morishima, H.; Takeuchi, T.; Umezawa, H.; Yamamoto, T. (Microbial Chemistry Research Foundation); Pharmacological cpd. with immunopotentiating activity and production and uses thereof. US 4238507 .
【3】 Arrigoni-Martelli, E.; Castaner, J.; Serradell, M.N.; Blancafort, P.; Forphenicinol. Drugs Fut 1983, 8, 7, 587.

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)	36152	methyl 4-(acetoxy)-3-hydroxybenzoate		C₁₀H₁₀O₅	详情	详情
(II)	36153	methyl 3-hydroxy-4-(hydroxymethyl)benzoate		C₉H₁₀O₄	详情	详情
(III)	10722	1-Methoxy-1-methylethyl methyl ether; 2,2-Dimethoxypropane	77-76-9	C₅H₁₂O₂	详情	详情
(IV)	36154	methyl 2,2-dimethyl-4H-1,3-benzodioxine-7-carboxylate		C₁₂H₁₄O₄	详情	详情
(VI)	36155	(2,2-dimethyl-4H-1,3-benzodioxin-7-yl)methanol		C₁₁H₁₄O₃	详情	详情
(VII)	36156	2,2-dimethyl-4H-1,3-benzodioxine-7-carbaldehyde		C₁₁H₁₂O₃	详情	详情
(VIII)	36157	2-amino-2-(2,2-dimethyl-4H-1,3-benzodioxin-7-yl)acetonitrile		C₁₂H₁₄N₂O₂	详情	详情

Extended Information