新产品编号:611161
Chemical Name: N-[3-(4-Methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-2-oxooxazolidin-5(S)-ylmethyl]acetamide
CAS No. 233773-46-1
项目整合开发状态: Preclinical
项目研究机构: Bayer (Originator)
合成路线:Benzoxazinone (IV) was prepared by condensation of 2-amino-5-nitrophenol (I) with either chloroacetyl chloride (II) in the presence of NaHCO3 or ethyl bromoacetate (III) in the presence of KF.Subsequent N-alkylation of (IV) with iodomethane provided (V).After reduction of the nitro group of (V) to amine (VI) by hydrogenation over Pd/C,condensation with benzyl chloroformate afforded carbamate (VII).The chiral oxazolidinone (IX) was obtained by reaction of (VII) with (-)-(R)-glycidyl butyrate (VIII) in the presence of butyllithium in THF at low temperature.Conversion of (IX) to mesylate,followed by displacement with NaN3 gave azide (X).Amine (XI) was then obtained by either hydrogenation of (X) over Pd/C or by reduction with trimethyl phosphite.Finally,reaction of (XI) with acetyl chloride and triethylamine provided the title acetamide.
📌 参考资料/链接：
参考文献标题:Novel bicyclene-substd.oxazolidinones
文献作者:Endermann,R.; H鋌ich,D.; Ruppelt,M.; Raddatz,S.; Rosentreter,U.; Riedl,B.; Bartel,S.; Wild,H.; Stolle,A.; Guarnieri,W.; Kroll,H.-P.(Bayer AG)
参考来源:DE 19802239; WO 9937641
📄 详细内容
合成路线:Benzoxazinone (IV) was prepared by condensation of 2-amino-5-nitrophenol (I) with either chloroacetyl chloride (II) in the presence of NaHCO3 or ethyl bromoacetate (III) in the presence of KF.Subsequent N-alkylation of (IV) with iodomethane provided (V).After reduction of the nitro group of (V) to amine (VI) by hydrogenation over Pd/C,condensation with benzyl chloroformate afforded carbamate (VII).The chiral oxazolidinone (IX) was obtained by reaction of (VII) with (-)-(R)-glycidyl butyrate (VIII) in the presence of butyllithium in THF at low temperature.Conversion of (IX) to mesylate,followed by displacement with NaN3 gave azide (X).Amine (XI) was then obtained by either hydrogenation of (X) over Pd/C or by reduction with trimethyl phosphite.Finally,reaction of (XI) with acetyl chloride and triethylamine provided the title acetamide.
参考文献标题:Synthesis and antibacterial activity of novel heteroaryl oxazolidinones: II.Benzoxazinone- and benzthiazinone-oxazolidinones
文献作者:Haebich,D.; Haerter,M.; Bartel,S.; Riedl,B.; Stolle,A.; Raddatz,S.; Kroll,H.P.; Guarnieri,W.; Endermann,R.; Wild,H.; Rosentreter,U.; Ruppelt,M.
参考来源:39th Intersci Conf Antimicrob Agents Chemother (Sept 26 1999,San Francisco) 1999,Abst F566
合成路线:Benzoxazinone (IV) was prepared by condensation of 2-amino-5-nitrophenol (I) with either chloroacetyl chloride (II) in the presence of NaHCO3 or ethyl bromoacetate (III) in the presence of KF.Subsequent N-alkylation of (IV) with iodomethane provided (V).After reduction of the nitro group of (V) to amine (VI) by hydrogenation over Pd/C,condensation with benzyl chloroformate afforded carbamate (VII).The chiral oxazolidinone (IX) was obtained by reaction of (VII) with (-)-(R)-glycidyl butyrate (VIII) in the presence of butyllithium in THF at low temperature.Conversion of (IX) to mesylate,followed by displacement with NaN3 gave azide (X).Amine (XI) was then obtained by either hydrogenation of (X) over Pd/C or by reduction with trimethyl phosphite.Finally,reaction of (XI) with acetyl chloride and triethylamine provided the title acetamide.
参考文献标题:A facile synthesis of 2-alkyl(aryl)-6- and -7-nitro-3-oxo-3,4-dihydro-2H-1,4-benzoxazines
文献作者:Shridhar,D.R.; et al.
参考来源:Synthesis 1982,986