药物详细合成路线
| Name | Sevoflurane;MR6S4;Ultane;Sevorane;Sevofrane | | Chemical Name | Fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ether | | CAS | 28523-86-6 | | Related CAS | | | Formula | C4H3F7O | | Structure |  | | Formula Weight | 200.05671 | | Stage | 上市-1990 | | Company | Maruishi Pharmaceutical (Originator), Dainippon Pharmaceutical (Not Determined), Abbott (Licensee), Kodama (Licensee), Abbott (Codevelopment) | | Activity/Mechanism | ANALGESIC AND ANESTHETIC DRUGS, Anesthetic Drugs, General Anesthetics, Inhalation Anesthetics | | Syn. Route | 4 | | Route 1 | | the synthesis of deuterated sevoflurane has been described:the methylation of 1,1,1,3,3,3-hexafluoroisopropanol (i) with deuterated dimethylsulfate by means of 10% aqueous naoh yields the corresponding deuterated methyl ether (ii), which is then fluorinated with brf3. | | |  | | List of intermediates | No. | | dodecanoyl chloride | (ii) | | 3-oxocyclohexanecarboxylic acid | (i) | | dibenzyl 2-[(1r)-3-oxocyclohexyl]malonate | (ii) | | | Reference 1: baker, m.t.; chiang, c.-k.; tinker, j.h.; synthesis of fluoro-dideutero-methyl 1,1,1,3,3,3-hexafluoro-2-propyl ether (deuterated sevoflurane). j label compd radiopharm 1993, 33, 9, 801. |
Route 2 | | 1,1,1,3,3,3-hexafluoro-2-propyl methyl ether (i) is photochlorinated with cl2 giving 1,1,1,3,3,3-hexafluoro-2-propylchloromethyl ether (ii), which is then fluorinated with kf in tetrahydrothiophene-1,1-dioxide. | | |  | | List of intermediates | No. | | dodecanoyl chloride | (i) | | 2-hydroxyethyl laurate | (ii) | | | Reference 1: regan, b.m.; longstreet, j.c.; halogenmethyl-1,3-polyhalogen-2-propyllathen und verfahren zu deren herstellung sowie diese enthaltende anasthesie-mittel. de 1954268; fr 2021695; gb 1250928; nl 6916076 . Reference 2: sungurbey, k.; castaner, j.; sevoflurane. drugs fut 1976, 1, 6, 307. |
Route 3 | | compound is obtained by reaction of 1,1,1,3,3,3-hexafluoro-2-propanol (i) with formaldehyde and hf in hot sulfuric acid. | | |  | | List of intermediates | No. | | 3-oxocyclohexanecarboxylic acid | (i) | | | Reference 1: coon, c.l.; simon, r.l. (baxter international inc.); method of synthesizing fluoromethylhexafluoroisopropyl ether. us 4469898 . |
Route 4 | | a new method for the preparation of sevoflurane has been described: reaction of 1,1,1,3,3,3-hexafluoro-2-propanol (i) with 1,3,5-trioxane (ii) and alcl3 gives the chloromethyl ether (iii), which is then fluorinated with kf in hot polyethylene glycol (peg-400). | | |  | | List of intermediates | No. | | 2-hydroxyethyl laurate | (iii) | | 3-oxocyclohexanecarboxylic acid | (i) | | 3-(2,3-dimethylphenoxy)phenyl methyl ether; 1-(3-methoxyphenoxy)-2,3-dimethylbenzene | (ii) | | | Reference 1: schure, r.m.; behme, c.; ramakrishma, k.; bieniarz, c.; a safe and efficient process for the synthesis of the inhalation anesthetic sevoflurane. org process res dev 2000, 4, 6, 581. |
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来源:药化网
作者:药化小编
摘要:本文合成路线介绍的是药物中文名七氟烷；英文名Sevoflurane;MR6S4;Ultane;Sevorane;Sevofrane；CAS[28523-86-6]
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