• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】69302

【品名】di-O-acetyl-L-tartaric acid anhydride;(3R,4R)-2,5-dioxotetrahydrofuran-3,4-diyl diacetate

【CA登记号】 

【 分 子 式 】C8H8O7

【 分 子 量 】216.147

【元素组成】C 44.45% H 3.73% O 51.81%

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:(VI)

Reduction of oxcarbazepine (I) using NaBH4 in ethanol/water yields the racemic alcohol (II), which is resolved into its enantiomers by means of fractional crystallization of the diastereomeric esters obtained from alcohol (II) and menthoxyacetyl chloride (III). Alkaline hydrolysis of the desired diastereoisomer (IV) provides the (S)-alcohol (V) , which is finally acylated with acetyl chloride and DMAP in pyridine/CH2Cl2 .
Condensation of racemic alcohol (II) with di-O-acetyl-L-tartaric acid anhydride (VI) – obtained by treatment of L-tartaric (VII) acid with hot AcO2 and trace H2SO4 – gives a disastereomeric mixture of tartrate monoesters (VIII), which is separated into diastereomeric alcohol esters by fractional crystallization in water and then the desired (S)-diastereomer hydrolyzed under alkaline conditions to afford alcohol (V) .

1 Benes, J., Vieira Araujo Soares da Silva, P.M. (Bial – Portela & Ca., SA). Substituted dihydrodibenzo[b,f]azepines, method of their preparation, their use in the treatment of some central nervous system disorders, and pharmaceutical compositions containing them. CA 2180301, EP 0751129, JP 1997110836, JP 2004256516, US 5753646, WO 199700250.
2 Benes, J., Parada, A., Figueiredo, A. et al. Anticonvulsant and sodium channel-blocking properties of novel 10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide derivatives. J Med Chem 1999, 42(14): 2582-7.
3 Learmonth, D.A. (Portela & Ca., SA). Method for preparation of (S)-(+)-and (R)-(-)-10,11-dihydro-10-hydroxy-5H, dibenz[b,f]azepine-5-carboxamide. CA 2447980, EP 1385826, GB 2377440, JP 2004534753, US 2004162280, US 2007073057, US 7119197, WO 2002092572.
4 Learmonth, D.A., Grasa, G.A., Zanotti-Gerosa, A. (Bial – Portela & Ca.,SA). Asymmetric catalytic reduction of oxcarbazepine. CA 2616984, EP 1915346, JP 2009502893, WO 2007012793.
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) 33774 10-oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide 28721-07-5 C15H12N2O2 详情 详情
(II) 58231 10-hydroxy-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide C15H14N2O2 详情 详情
(III) 33776 2-[[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy]acetyl chloride 15356-62-4 C12H21ClO2 详情 详情
(IV) 33777 (10S)-5-(aminocarbonyl)-10,11-dihydro-5H-dibenzo[b,f]azepin-10-yl 2-[[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy]acetate C27H34N2O4 详情 详情
(V) 33775 (10S)-10-hydroxy-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide C15H14N2O2 详情 详情
(VI) 69302 di-O-acetyl-L-tartaric acid anhydride;(3R,4R)-2,5-dioxotetrahydrofuran-3,4-diyl diacetate   C8H8O7 详情 详情
(VII) 28379 (2R,3R)-2,3-dihydroxybutanedioic acid; L-Tartaric acid; (2R,3R)-2,3-dihydroxysuccinic acid 87-69-4 C4H6O6 详情 详情
(VIII) 69303 (2S,3S)-4-((5-carbamoyl-10,11-dihydro-5H-dibenzo[b,f]azepin-10-yl)oxy)-2,3-dihydroxy-4-oxobutanoic acid   C19H18N2O7 详情 详情
Extended Information