NSC-708199
Chemical Name: (+)-2-Methyl-3(S)-(3-methylphenyl)-2,3-dihydro-1,2-benzisothiazole 1,1-dioxide
CAS No. 256221-01-9, 256221-00-8 (racemate)
项目整合开发状态: Biological Testing
项目研究机构: University of Tennessee, Knoxville (Originator)
合成路线:Reaction of benzenesulfonyl chloride (I) with methylamine afforded sulfonamide (II).Regioselective ortho lithiation of (II) with n-butyllithium,followed by condensation with 3-methylbenzaldehyde (III) gave carbinol (IV),which was cyclized to the sultam (V) by treatment with concentrated H2SO4.The desired (S)-enantiomer was finally isolated by chiral HPLC.
📌 参考资料/链接：
参考文献标题:Methods of synthesizing sultams and anti-viral compsns.
文献作者:Johnson,S.C.; Yan,S.; Mayasundari,A.; Mao,J.; Baker,D.C.(University of Tennessee,Knoxville)
参考来源:WO 0004004
📄 详细内容
合成路线:An enantioselective synthesis of the desired (S)-isomer was further developed starting from saccharin (VI).After conversion to the magnesium amide enolate (VII) by means of phenylmagnesium bromide,addition of Grignard reagent (VIII) produced the aryl sulfonimide (IX).Enantioselective reduction to the (S)-sulfonamide (X) was then accomplished using a chiral rhodium catalyst.Then,N-methylation of (X) with yodomethane in the presence of Cs2CO3 provided the title compound.
参考文献标题:Synthesis and molecular modeling studies of 3-aryl-2-methyl-2,3-dihydrobenzo[d]isothiazole 1,1-dioxides: Nonnucleoside reverse transcriptase inhibitors of HIV-1
文献作者:Condo,A.M.; et al.
参考来源:219th ACS Natl Meet (March 26 2000,San Francisco) 2000,Abst MEDI 124