RESOLUTION OF HYDROXYUREAS

被引:10
作者
GARIGIPATI, RS
SORENSON, ME
ERHARD, KF
ADAMS, JL
机构
[1] Department of Medicinal Chemistry, SmithKline Beecham Pharmaceuticals, King of Prussia, PA 19046
关键词
D O I
10.1016/S0040-4039(00)73875-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Racemic hydroxyureas can be efficiently resolved on a preparative scale using (4S)-4-benzyl-2-oxazolidinone-3-carbonyl chloride 3. The resulting carbamates can be separated by chromatography and hydrolysis of these diastereomers yields enantiomerically pure hydroxyureas.
引用
收藏
页码:5537 / 5540
页数:4
相关论文
共 10 条
[1]   CONTRASTERIC CARBOXIMIDE HYDROLYSIS WITH LITHIUM HYDROPEROXIDE [J].
EVANS, DA ;
BRITTON, TC ;
ELLMAN, JA .
TETRAHEDRON LETTERS, 1987, 28 (49) :6141-6144
[2]   ASYMMETRIC ALKYLATION REACTIONS OF CHIRAL IMIDE ENOLATES - A PRACTICAL APPROACH TO THE ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED CARBOXYLIC-ACID DERIVATIVES [J].
EVANS, DA ;
ENNIS, MD ;
MATHRE, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (06) :1737-1739
[3]  
GARLAND L G, 1991, Drugs of the Future, V16, P547
[4]  
Gleason JG, 1986, ANNU REP MED CHEM, V21, P73
[5]   SYNTHESIS OF CHIRAL ZILEUTON, A POTENT AND SELECTIVE INHIBITOR OF 5-LIPOXYGENASE [J].
HSIAO, CN ;
KOLASA, T .
TETRAHEDRON LETTERS, 1992, 33 (19) :2629-2632
[6]  
MASAMUNE H, 1989, ANNU REP MED CHEM, V24, P71
[7]   LEUKOTRIENES - MEDIATORS OF IMMEDIATE HYPERSENSITIVITY REACTIONS AND INFLAMMATION [J].
SAMUELSSON, B .
SCIENCE, 1983, 220 (4597) :568-575
[8]  
SHAW A, 1990, ANNU REP MED CHEM, V25, P61
[9]   STRUCTURE-ACTIVITY ANALYSIS OF A CLASS OF ORALLY ACTIVE HYDROXAMIC ACID INHIBITORS OF LEUKOTRIENE BIOSYNTHESIS [J].
SUMMERS, JB ;
GUNN, BP ;
MARTIN, JG ;
MARTIN, MB ;
MAZDIYASNI, H ;
STEWART, AO ;
YOUNG, PR ;
BOUSKA, JB ;
GOETZE, AM ;
DYER, RD ;
BROOKS, DW ;
CARTER, GW .
JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (10) :1960-1964
[10]   PREPARATIVE SEPARATION AND ANALYSIS OF THE ENANTIOMERS OF [C-14] ZILEUTON, A 5-LIPOXYGENASE INHIBITOR [J].
THOMAS, SB ;
SURBER, BW ;
FITZGERALD, M .
JOURNAL OF CHROMATOGRAPHY, 1992, 623 (02) :390-394