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【结 构 式】 
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【药物名称】Sulotroban, SK&F-95587, BM-13177 【化学名称】[4-[2-[(Phenylsulfonyl)amino]ethyl]phenoxy]acetic acid 【CA登记号】72131-33-0 【 分 子 式 】C16H17NO5S 【 分 子 量 】335.38159 |
【开发单位】Roche (Originator) 【药理作用】Antiplatelet Therapy, Coagulation Disorders Therapy, HEMATOLOGIC DRUGS, Prostanoid TP (Thromboxane A2) Antagonists |
合成路线1
The reaction of 4-[2-(acetylamino)ethyl]phenol (I) with ethyl bromoacetate (II) by means of K2CO3 in refluxing butanone gives 4-[2-(acetylamino)ethyl]phenoxyacetic acid ethyl ester (III), which is hydrolyzed with refluxing aqueous HCl to 4-(2-aminoethyl)phenoxyacetic acid (IV). Finally, this compound is acylated with benzenesulfonyl chloride (V) by means of K2CO3 in hot water.
| 【1】 Witte, E.C.; Wolff, H.P.; Thiel, M.; Stegmeier, K.; Roesch, E.; Phenoxyalkylcarboxylic acid compounds and thrombocyte-aggregation inhibition. DE 2809377; EP 0004011; ES 478228; JP 54122250; US 4258058 . |
| 【2】 Karup, G.L.; Preikschat, H.F. (GEA A/S Farmaceutisk Fabrik); Process for the preparation of 1,4-dihydropyridines and cpds. used in this process. WO 9925688 . |
| 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) | 19989 | N-(4-hydroxyphenethyl)acetamide | C10H13NO2 | 详情 | 详情 | |
| (II) | 16640 | Ethyl 2-bromoacetate; Ethyl bromoacetate | 105-36-2 | C4H7BrO2 | 详情 | 详情 |
| (III) | 34332 | ethyl 2-[4-[2-(acetamido)ethyl]phenoxy]acetate | C14H19NO4 | 详情 | 详情 | |
| (IV) | 34333 | 2-[4-(2-aminoethyl)phenoxy]acetic acid | C10H13NO3 | 详情 | 详情 | |
| (V) | 14713 | benzenesulfonyl chloride | 98-09-9 | C6H5ClO2S | 详情 | 详情 |
Extended Information