137382-38-8
2-(tert-Butyldimethylsilyl)thiazole
CAS: 137382-38-8
Molecular Formula: C9H17NSSi
137382-38-8 - Names and Identifiers
| Name | 2-(tert-Butyldimethylsilyl)thiazole |
| Synonyms | 2-(tert-Butyldimethylsilyl) 2-(t-Butyldimethylsilyl)Thiazole 2-(tert-Butyldimethylsilyl)thiazole tert-butyl-dimethyl-(2-thiazolyl)silane 2-(tert-butyldiMethylsilyl)-1,3-thiazole 2-[tert-Butyl(dimethyl)silyl]-1,3-thiazole Thiazole, 2-[(1,1-dimethylethyl)dimethylsilyl]- |
| CAS | 137382-38-8 |
| InChI | InChI=1/C9H17NSSi/c1-9(2,3)12(4,5)8-10-6-7-11-8/h6-7H,1-5H3 |
137382-38-8 - Physico-chemical Properties
| Molecular Formula | C9H17NSSi |
| Molar Mass | 199.39 |
| Density | 0.96 |
| Boling Point | 219 ºC |
| Flash Point | 86 ºC |
| Vapor Presure | 0.178mmHg at 25°C |
| Storage Condition | 2-8℃ |
| Refractive Index | 1.4990-1.5030 |
| MDL | MFCD10699169 |
137382-38-8 - Reference Information
| overview | AHU377 and angiotensin IIAT1 receptor antagonist valsartan form LCZ696 in a 1:1 molar ratio, LCZ696 is a dual inhibitor of angiotensin II(AT2) receptor and enkephalinase (Neprilysin) receptor, and its antihypertensive effect is better than standard antihypertensive drugs, it is a new type of drug for the treatment of heart failure. AHU377 is a prodrug that can convert the active form of enzyme cleavage LBQ657 ethyl ester. At present, the efficacy and safety of this drug in milestone phase III exceed the clinical standard drug enalapril, and the most important intermediate of AHU377 is 2-(tert-butyl dimethylsilyl) thiazole. |
| application | 2-(tert-butyl dimethylsilyl) thiazole is mainly used as a pharmaceutical intermediate and a key intermediate for preparing drugs for chronic heart failure. |
| Preparation | a)L-serine methyl ester hydrochloride first reacts with BOC anhydride, then reacts with tert-butyldimethylchlorosilane to form 2-(tert-butyldimethylsilyl) thiazole; B) N-(tert-butoxycarbonyl)-O-(tert-butyldimethylsilyl)-L-serine methyl ester is reduced with sodium borohydride to form tert-butyl (R)-(1-((tert-butyldimethylsilyl) oxy)-3-hydroxypropyl-2-yl) carbamic acid; c) tert-butyl (R)-(1-((tert-butyl dimethylsilyl) oxy)-3-hydroxypropyl-2-yl) carbamic acid reacts with thionyl chloride, and is then oxidized by ruthenium chloride trihydrate and sodium periodate to form a compound of formula A. Unless otherwise specified, the characteristics of the reaction elements involved in steps a), B) and c) above are carried out by technical means available in the prior art. In step a), organic bases are also used in the reaction with BOC anhydride. The organic base is used to neutralize the acid produced by the reaction process. Such as adding triethylamine, diisopropylethylamine, 4-dimethylaminopyridine, inorganic potassium carbonate, sodium carbonate, sodium bicarbonate. Preferably, triethylamine is used. The reaction with BOC anhydride in step a) also uses a solvent. The solvent is an organic solvent, which is an oil as a reaction medium. The solvent is selected from one or more of ethyl acetate, tetrahydrofuran and dichloromethane. Preferably, the solvent is dichloromethane. Preferably, in step a), the reaction temperature of the reaction with the BOC anhydride is -5-80°C. More preferably, in step a), the reaction temperature of the reaction with the BOC anhydride is 10-25°C. More preferably, after the reaction with BOC anhydride is finished, the organic phase is washed and dried by suction filtration, water addition and liquid separation. The reaction with tert-butyldimethylchlorosilane is also added with an organic base selected from one or more of triethylamine, diisopropylethylamine and imidazole. Preferably, the organic base is imidazole. The organic base is used to neutralize the acid produced in the reaction of step a). A solvent is also used in the reaction with tert-butyldimethylchlorosilane; the solvent is preferably dichloromethane. The reaction temperature in the reaction with tert-butyldimethylchlorosilane is -5~80 ℃. Preferably -5 to 5°C. More preferably 0°C. After the end of step a), a post-processing step is also included. Generally, the post-treatment is a quenching reaction using hydrochloric acid, separating the liquid, extracting the aqueous phase with dichloromethane, combining the organic phase, drying, and removing the solvent. In step B), the reaction temperature of the reaction is -40-10°C. More preferably, the reaction temperature is from 0 to 10°C. In step B), a solvent is also used in the reaction, and the solvent is selected from one or more of tetrahydrofuran, methanol and ethanol. Preferably, the solvent is ethanol. The solvent is an organic solvent and is an oil liquid as a reaction medium. In step B), sodium borohydride is added to the reaction system in batches. More preferably, the solvent in step B) is selected from one or more of tetrahydrofuran, methanol and ethanol. Preferably, in step B), a post-treatment process is further included after the reaction. Used to separate products. Such as extraction, washing, drying and concentration processes. In step c), the reaction system further includes a solvent, and the solvent is an organic solvent, which is an oil as a reaction medium. More preferably, the solvent is selected from one or more of ethyl acetate, tetrahydrofuran or dichloromethane. More preferably, the solvent is dichloromethane. In step c), the reaction post-treatment process is also included. used to isolate the target product. Such as washing, drying and separation and other post-treatment techniques. The reaction temperature in step c) is -50~30 ℃. After the reaction with thionyl chloride in step c) is finished, a post-treatment step is also included. The post-treatment step includes water quenching reaction, liquid separation and organic phase washing. Before reacting with ruthenium chloride trihydrate, it also includes the step of adding sodium periodate aqueous solution. Preferably, the concentration of the sodium periodate aqueous solution is 10%. The reaction temperature of the reaction with ruthenium chloride trihydrate in step c) is -50~0 ℃. |
Last Update：2024-04-09 20:49:11
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