专利号:US-4383949-A 优先权日:1980-07-16 标题:Preparation of 3-bromo-4-fluorobenzaldehyde and its acetals 发明人:MAURER FRITZ; RIEBEL HANS-JOCHEM; PRIESNITZ UWE; KLAUKE ERICH 权利人:BAYER AG 摘要:A process for the preparation of a 3-bromo-4-fluorobenzaldehyde acetal of the formula ##STR1## in which R 1 is methyl or ethyl, n which comprises reacting a 3-bromo-4-fluoro-benzoic acid halide with ammonia to form 3-bromo-4-fluoro-benzoic acid amide, dehydrating said amide to form 3-bromo-4-fluoro-benzonitrile, reacting the nitrile with formic acid in the presence of a catalyst at a temperature between about 0° and 150° C. to form 3-bromo-4-fluorobenzaldehyde, and reacting said aldehyde with R 1 OH or a derivative thereof capable of forming an acetal. The amide and nitrile are new compounds. The acetals are known intermediates in the synthesis of pyrethroid-like insecticides.
专利号:US-4283531-A 优先权日:1978-06-02 标 题:Synthesis of β-lactams having a substituted hydroxymethylene group at the position α to the lactam carbonyl group 发明人:GANGULY ASHIT K; GIRIJAVALLABHAN VIYYOOR M; CAVENDER PATRICIA; SARRE OLGA; MCCOMBIE STUART W 权利人:SCHERING CORP 摘要:β-Lactams having a substituted hydroxymethylene group at the position α to the lactam carbonyl group are prepared by reaction of an α-halo-β-lactam with zinc or zinc amalgam in an anhydrous aprotic medium to produce an intermediate which in situ reacts with an appropriate aldehyde or ketone. n Also described are novel penicillins and cephalosporins having useful antibacterial activity.
专利号:US-4468351-A 优先权日:1983-06-06 标题 :Process for debromination of dibromopenicillanic acid and derivatives 发明人:PIRIE DONALD K; WEEKS PAUL D 权利人:PFIZER 摘要:A process for the debromination of 6-monobromo- and 6,6-dibromopenicillanic acid, and various derivatives thereof, by the action of a bisulfite salt. The debrominated compounds produced find various utilities, as beta-lactamase inhibitors useful in therapy in combination with known beta-lactam antibiotics, or as intermediates in the further synthesis of useful beta-lactam compounds.
参考标题:Synthesis Of (5R)-(Z)-6-(1-Methyl-1,2,3-Triazol-4-Ylmethylene)Penem-3-Carboxylic Acid, A Potent Broad Spectrum β-Lactamase Inhibitor, From 6-Aminopenicillanic Acid 作者:Neal F. Osborne,Richard J. Atkins,Nigel J. P. Broom,Steven Coulton,John B. Harbridge,Michael A. Harris,Irene Stirling-François,Graham Walker 摘要:(5R)-(Z)-6-(1-Methyl-1,2,3-Triazol-4-Ylmethylene)Penem-3-Carboxylic Acid 34 (Brl 42715) Has Been Prepared From 6-Aminopenicillanic Acid 4 (6-Apa) By A Short, Stereoselective And Efficient Route Via The Novel Intermediate. P-Methoxybenzyl (5R,6S)-6-Bromopenem-3-Carboxylate 17.Elaboration Of 6-Apa 4 To The Azetidinone Disulfide 10 By Established Methodology, Followed By Reductive Formylation Provided The Crystalline C-4 Formylthio-Azetidinone Derivative 29. Cyclization Of The Oxalimide 28, Obtained By Ozonolysis Of The Formylthio Derivative 29. To The Crystalline 6 Alpha-Bromopenem Ester 17 Was Effected By Way Of The Phosphite-Mediated Carbonyl-Carbonyl Coupling Reaction.