Synthesis and Determination of Absolute Configuration of (R)-(+)-5-{4-[2-(5-Chloroindazol-2-yl)ethoxy]benzyl}- 5-methyl-2,4-oxazolidinedione

Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (08): 1254-1258. Previous Articles Next Articles

Original Articles

(R)-(＋)-5-甲基-5-{4-[2-(2-(5-氯吲唑基))乙氧基]苄基}-2,4-噁唑烷二酮的合成及其绝对构型的确定

李雅潇^a; 马慧勇^a ; 林紫云^a; 王经斌^a; 杨世颖^a ;
张艳红^b ; 吕扬^a; 黄海洪^*,a

(a中国医学科学院中国协和医科大学药物研究所北京 100050)
(b国家新药开发工程技术研究中心北京 102600)

收稿日期:2009-03-17 修回日期:2009-04-27 发布日期:2009-08-30
通讯作者: 黄海洪

Synthesis and Determination of Absolute Configuration of (R)-(+)-5-{4-[2-(5-Chloroindazol-2-yl)ethoxy]benzyl}- 5-methyl-2,4-oxazolidinedione

Li, Yaxiao^a; Ma, Huiyong^a; Lin, Ziyun^a; Wang, Jingbin^a; Yang, Shiying^a;
Zhang, Yanhong^b ; Lü, Yang^a; Huang, Haihong^*,a

(a Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050) (b National Engineering Research Center for the Development of New Drugs, Beijing 102600)

Received:2009-03-17 Revised:2009-04-27 Published:2009-08-30
Contact: Huang, Haihong

Abstract

The chiral α-hydroxyester 4 was obtained by acid catalyzed esterification of the corresponding α-hydroxylacid that was resolved by (S)-(－)-1-phenylethylamine. After cyclization and deprotection, the key intermediate (R)-(＋)-5-methyl-5-(4-hydroxybenzyl)-2,4-oxazolidinedione (6) was obtained. The novel title compound 9 was obtained by the condensation of 6 with methanesulfonate 8. The structure of 9 was confirmed by 1H NMR and HRMS techniques, and its absolute configuration was derived from the X-ray diffraction of R enantiomer of 3.

Key words: chemical resolution, single-crystal X-ray diffraction, absolute configuration, 2,4-oxazolidinedione

Cite this article

Li, Yaxiao^a; Ma, Huiyong^a; Lin, Ziyun^a; Wang, Jingbin^a; Yang, Shiying^a;
Zhang, Yanhong^b ; Lü, Yang^a; Huang, Haihong^*,a
. Synthesis and Determination of Absolute Configuration of (R)-(+)-5-{4-[2-(5-Chloroindazol-2-yl)ethoxy]benzyl}- 5-methyl-2,4-oxazolidinedione[J]. Chin. J. Org. Chem., 2009, 29(08): 1254-1258.

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(R)-(＋)-5-甲基-5-{4-[2-(2-(5-氯吲唑基))乙氧基]苄基}-2,4-噁唑烷二酮的合成及其绝对构型的确定

Synthesis and Determination of Absolute Configuration of (R)-(+)-5-{4-[2-(5-Chloroindazol-2-yl)ethoxy]benzyl}- 5-methyl-2,4-oxazolidinedione

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