SYNTHESIS OF AMIDES - AN EFFICIENT AND CHEMOSELECTIVE METHOD FOR THE PREPARATION OF BETA-LACTAM DERIVATIVES RELATED TO HLE INHIBITORS

被引:6
作者
DIFABIO, R [1 ]
SUMMA, V [1 ]
ROSSI, T [1 ]
机构
[1] GLAXO RES,I-37100 VERONA,ITALY
关键词
D O I
10.1016/S0040-4020(01)80373-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical method for the chemoselective synthesis of amides in presence of the beta-lactam ring has been described, by an efficient coupling reaction between a reactive 2-pyridyl thiolester intermediate and a suitable N-silylamine.
引用
收藏
页码:2299 / 2306
页数:8
相关论文
共 24 条
[11]   PH3P-(PYS)2-CH3CN AS AN EXCELLENT CONDENSING SYSTEM FOR BETA-LACTAM FORMATION FROM BETA-AMINO ACIDS [J].
KOBAYASHI, S ;
IIMORI, T ;
IZAWA, T ;
OHNO, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (09) :2406-2408
[12]   TOTAL SYNTHESIS OF ECHINOCANDINS .2. TOTAL SYNTHESIS OF ECHINOCANDIN-D VIA EFFICIENT PEPTIDE COUPLING REACTIONS [J].
KUROKAWA, N ;
OHFUNE, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) :6043-6045
[13]  
Larock RC, 1989, COMPREHENSIVE ORGANI, P972
[14]   AMINO-ACIDS AND PEPTIDES .34. ANCHIMERICALLY ASSISTED COUPLING REACTIONS - USE OF 2-PYRIDYL THIOLESTERS [J].
LLOYD, K ;
YOUNG, GT .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (17) :2890-&
[15]  
MITMAN C, 1972, PULMONARY EMPHYSEMA, P1
[16]   PEPTIDE SYNTHESIS VIA OXIDATION-REDUCTION CONDENSATION BY USE OF NON-METALLIC COMPOUND AS A MERCAPTAN SCAVENGER [J].
MUKAIYAMA, T ;
MATSUEDA, R ;
MARUYAMA, H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1970, 43 (04) :1271-+
[17]  
MUKAIYAMA T, 1970, TETRAHEDRON LETT, V22, P1901
[18]   CHEMISTRY OF CEPHALOSPORIN ANTIBIOTICS .18. SYNTHESIS OF 7-ACYL-3-METHYL-2-CEPHEM-4-CARBOXYLIC ACID ESTERS [J].
MURPHY, CF ;
KOEHLER, RE .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (07) :2429-&
[19]  
Patai S., 1991, CHEM SILICON HETEROA, P365
[20]   INHIBITION OF HUMAN-LEUKOCYTE ELASTASE .3. SYNTHESIS AND ACTIVITY OF 3'-SUBSTITUTED CEPHALOSPORINS [J].
SHAH, SK ;
BRAUSE, KA ;
CHANDLER, GO ;
FINKE, PE ;
ASHE, BM ;
WESTON, H ;
KNIGHT, WB ;
MAYCOCK, AL ;
DOHERTY, JB .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2529-2535