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【结 构 式】 
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【分子编号】20251 【品名】2-[(isocyanatosulfonyl)oxy]-1,3-diisopropylbenzene 【CA登记号】 |
【 分 子 式 】C13H17NO4S 【 分 子 量 】283.34832 【元素组成】C 55.11% H 6.05% N 4.94% O 22.59% S 11.32% |
合成路线1
该中间体在本合成路线中的序号：(X)1) The reaction of (V) with SOCl2 or (COCl)2 in DMF affords the expected acyl chloride (VI), which is finally condensed with 2,6-diisopropylphenyl sulfamate (VII) by means of triethylamine in hot toluene to obtain Avasimibe. 2) The sulfamate (VII) can be obtained by condensation of 2,6-diisopropylphenol (VIII) with chlorosulfonyl isocyanate (IX) in refluxing toluene to give the isocyanate (X), which is hydrolyzed with water to the sulfamate (VII). compound is condensed with the previously described isocyanate (X) in refluxing THF to obtain Avasimibe. 3) Avasimibe can also be obtained by condensation of isocyanate (X) with Grignard reagent (XIII).
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【1】
Sorbera, L.A.; Rabasseda, X.; Castañer, J.; Avasimibe |
| 【2】 Lee, H.T.; Picad, J.A.; Sliskovic, D.R.; Wierenga, W. (Pfizer Inc.); N-Acyl sulfamic acid esters (or thioesters), N-acyl sulfonamides, and N-sulfonyl carbamic acid esters (or thioesters) as hypercholesterolemic agents. EP 0698010; JP 1996510256; US 5491172; WO 9426702 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 20240 | 2-(2,4,6-triisopropylphenyl)acetic acid | C17H26O2 | 详情 | 详情 | |
| (VI) | 20247 | 2-(2,4,6-triisopropylphenyl)acetyl chloride | C17H25ClO | 详情 | 详情 | |
| (VII) | 20248 | 2,6-diisopropylphenylsulfamate | C12H19NO3S | 详情 | 详情 | |
| (VIII) | 20249 | 2,6-Diisopropylphenol | 2078-54-8 | C12H18O | 详情 | 详情 |
| (IX) | 14101 | Chlorosulfonyl isocyanate | 1189-71-5 | CClNO3S | 详情 | 详情 |
| (X) | 20251 | 2-[(isocyanatosulfonyl)oxy]-1,3-diisopropylbenzene | C13H17NO4S | 详情 | 详情 | |
| (XIII) | 20243 | bromo(2,4,6-triisopropylbenzyl)magnesium | C16H25BrMg | 详情 | 详情 |