Home

Citation: SHA Lan-Lan, LIANG Wei-Zhou, CHEN Xin-Zhia. Synthesis of Sitaxsentan Sodium[J]. Chinese Journal of Applied Chemistry, ;2007, 24(11): 1310-1313. shu

Synthesis of Sitaxsentan Sodium

1.
a College of Materials Science and Chemical Engineering, Zhejiang University, Hangzhou 310027;
2.
b Discovery ChemScience Co. Ltd, Zhuhai

Corresponding author: CHEN Xin-Zhia,
Received Date: 21 October 2006
Available Online: 6 February 2007

The optimized synthesis route and process conditions of Sitaxsentan sodium were reported. 4-Methyl-pyrocatechol(1) reacted with dichloromethane(2) to give 5-methy 1-benzparallel[d][1,3]dioxolene(3), then chloromethylated into 5-chloromethyl-6-methyl-benzparallel[d][1,3]dioxolene(5), compound 5 reacted with magnesium(6) to obtain Grignard reagent(7). Sitaxsentan(9) was obtained through the reaction of N-methoxyl-N-methyl-3-[(4-chloro-3-methyl-5-isoxazole)-sulfamido]-2-thenylamide(Weinreb amide)(8) with Grignard reagent 7 in the presence of an acid, and Sitaxsentan sodium(10) was finally obtained from saturated dicarbonate solution. The structure of the product was proved by nuclear magnetic resonance analysis. The overall yield of compound 9 is 52.6%, and that of compound 10 is 54.2%. The optimal temperature of synthesizing compound 3 is 100℃ and tetrabutylammonium chloride accelerates the synthesis reaction of compound 3 as catalyst.The by-product was not obtained by using tetrabutylammonium chloride in place of tetrabutylammonium bromide as catalyst of synthesizing compound 5. The reaction time was reduced and the cost was decreased by changing the molar ratio of raw material and reaction order when compounds 9 and 10 were synthesized.
- Weinreb Amide,
- methyl-benzparallel[d][1,3]dioxolene,
- chloromethyl-methyl-benzparallel[d][1,3]dioxolene,
- sitaxsentan
1. [1]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
2. [2]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
3. [3]
  Meijin Li , Xirong Fu , Xue Zheng , Yuhan Liu , Bao Li . The Marvel of NAD⁺: Nicotinamide Adenine Dinucleotide. University Chemistry, 2024, 39(9): 35-39. doi: 10.12461/PKU.DXHX202401027
4. [4]
  Mengyang LI , Hao XU , Zhonghao NIU , Chunhua GONG , Weihui ZHONG , Jingli XIE . Highly effective catalytic synthesis of β-amino alcohols by using viologen-polyoxometalate hybrid materials. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1294-1300. doi: 10.11862/CJIC.20250080
5. [5]
  Hailang JIA , Pengcheng JI , Hongcheng LI . Preparation and performance of nickel doped ruthenium dioxide electrocatalyst for oxygen evolution. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1632-1640. doi: 10.11862/CJIC.20240398
6. [6]
  He Yao , Wenhao Ji , Yi Feng , Chunbo Qian , Chengguang Yue , Yue Wang , Shouying Huang , Mei-Yan Wang , Xinbin Ma . Copper-catalyzed and biphosphine ligand controlled 3,4-boracarboxylation of 1,3-dienes with carbon dioxide. Chinese Chemical Letters, 2025, 36(4): 110076-. doi: 10.1016/j.cclet.2024.110076
7. [7]
  Yanfen PENG , Xinyue WANG , Tianbao LIU , Xiaoshuo WU , Yujing WEI . Syntheses and luminescence of four Cd(Ⅱ)/Zn(Ⅱ) complexes constructed by 1,3‐bis(4H‐1,2,4‐triazole)benzene. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1416-1426. doi: 10.11862/CJIC.20250018
8. [8]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
9. [9]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
10. [10]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
11. [11]
  Wei HE , Jing XI , Tianpei HE , Na CHEN , Quan YUAN . Application of solar-driven inorganic semiconductor-microbe hybrids in carbon dioxide fixation and biomanufacturing. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 35-44. doi: 10.11862/CJIC.20240364
12. [12]
  Zongsheng LI , Yichao WANG , Yujie WANG , Wenhao ZHU , Xiaoyao YIN , Wudan YANG , Songzhi ZHENG , Weihai SUN . Preparation of CsPbBr₃ perovskite solar cells via bottom interface modification with methylammonium chloride. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1805-1816. doi: 10.11862/CJIC.20250066
13. [13]
  Shiyi WANG , Chaolong CHEN , Xiangjian KONG , Lansun ZHENG , Lasheng LONG . Polynuclear lanthanide compound [Ce₄^ⅢCe₆^Ⅳ(μ₃-O)₄(μ₄-O)₄(acac)₁₄(CH₃O)₆]·2CH₃OH for the hydroboration of amides to amine. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 88-96. doi: 10.11862/CJIC.20240342
14. [14]
  Ze Luo , Yukun Zhu , Yadan Luo , Guangmin Ren , Yonghong Wang , Hua Tang . Photocatalytic selective oxidation of 5-hydroxymethylfurfural coupled with H₂ evolution over In₂O₃/ZnIn₂S₄ S-scheme heterojunction. Acta Physico-Chimica Sinica, 2026, 42(3): 100166-0. doi: 10.1016/j.actphy.2025.100166
15. [15]
  Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980
16. [16]
  Xiaolong Li , Shiqi Zhong , Xiangfeng Wei , Zhiqiang Liu , Pan Zhan , Jiehua Liu . Carbon Dioxide: From the Past to the Future. University Chemistry, 2026, 41(2): 242-247. doi: 10.12461/PKU.DXHX202503013
17. [17]
  Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α_1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
18. [18]
  Aiyi Xin , Jiawei Li , Xinyang Ran , Chuanjiang Fu , Zhiguo Wang . Collaborative Science and Education Based Experimental Design in Organic Chemistry: A Case Study of the Nucleophilic Substitution Reaction of 2-Hydroxymethyl-4,6-Di-Tert-Butylphenol. University Chemistry, 2025, 40(5): 366-375. doi: 10.12461/PKU.DXHX202407031
19. [19]
  Yihui Song , Shangshang Qin , Kai Wu , Chengyun Jin , Bin Yu . 生物化学在高水平创新型药学人才培养中的交叉融合应用——以去甲基化酶LSD1抑制剂的活性评价为例. University Chemistry, 2025, 40(6): 341-352. doi: 10.12461/PKU.DXHX202406018
20. [20]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-0. doi: 10.3866/PKU.WHXB202309027

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(773)
HTML views(126)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return