新产品编号:1198083
Chemical Name:
项目整合开发状态: Biological Testing
项目研究机构: Ohio State University (Originator)
合成路线:Nitration of 2-hydroxy-DL-phenylalanine (I) with nitronium tetrafluoroborate in cooled acetonitrile provided the dinitro compound (II),which was isolated through a cation exchange column as the ammonium phenolate salt.Acylation under Schotten Baumann conditions gave racemic acetamide (III).Then,kinetic resolution with Aspergillus acylase I produced the desired (S)-amine together with unaltered (R)-acetamide (IV),which were separated by partition between water and ethyl acetate.The organic extract provided (S)-amine with an optical purity of > 99% e.e.
📌 参考资料/链接：
参考文献标题:Design and synthesis of enantiomers of 3,5-dinitro-o-tyrosine: alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropanoic acid (AMPA) receptor antagonists
文献作者:Sun,G.; Slavica,M.; Uretsky,N.J.; Wallace,L.J.; Shams,G.; Weinstein,D.M.; Miller,J.C.; Miller,D.D.
参考来源:J Med Chem 1998,41(7),1034-1041
📄 详细内容
合成路线:Nitration of 2-hydroxy-DL-phenylalanine (I) with nitronium tetrafluoroborate in cooled acetonitrile provided the dinitro compound (II),which was isolated through a cation exchange column as the ammonium phenolate salt.Acylation under Schotten Baumann conditions gave racemic acetamide (III).Then,kinetic resolution with Aspergillus acylase I produced the desired (S)-amine together with unaltered (R)-acetamide (IV),which were separated by partition between water and ethyl acetate.The organic extract provided (S)-amine with an optical purity of > 99% e.e.
参考文献标题:Structure-activity studies for alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropanoic acid receptors: Acidic hydroxyphenylalanines
文献作者:Hill,R.A.; Wallace,L.J.; Miller,D.D.; Weinstein,D.M.; Shams,G.; Tai,H.L.; Layer,R.T.; Willins,D.; Uretsky,N.J.; Danthi,S.N.
参考来源:J Med Chem 1997,40(20),3182-3191