The Development of the New Processes for Manufacturing the Key Intermediates of .BETA.-Lactam Antibiotics

Autor:	Hidenori Kumobayashi, Takashi Miura, Noboru Sayo, Takao Saito
Rok vydání:	1999
Předmět:	chemistry.chemical_compound Addition reaction chemistry Organic Chemistry Asymmetric hydrogenation Lactam chemistry.chemical_element Medicinal chemistry Hydroformylation Rhodium Palladium Ruthenium Catalysis
Zdroj:	Journal of Synthetic Organic Chemistry, Japan. 57:387-393
ISSN:	1883-6526 0037-9980
DOI:	10.5059/yukigoseikyokaishi.57.387
Popis:	It is well-known that (3R, 4R) -4-acetoxy-3- [(R) -1'- ((t-butyldimethylsilyl) oxy) ethyl] -2-azetidinone (4-AA) and (3S, 4S) - [(R) -1'- (t-butyldimethylsilyl) oxyethyl] -4- (R) -1-carboxyethyl-2-azetidinone (1β-methylcarboxylic acid) are very important intermediates for the synthesis of carbapenems and 1β-methyl carbapenems.We have developed the industrial processes for the syntheses of these intermediates. The synthesis of 4-AA was accomplished by the use of the ruthenium-BINAP complex catalyzed asymmetric hydrogenation of methyl 2-benzamidomethyl-3-oxobutanoate followed by the cyclization to β-lactam and the ruthenium catalyzed acetoxylation of β-lactam as the key technologies. In addition, for the synthesis of 1β-methylcarboxylic acid, we have developed three processes which involve a palladium catalyzed deallyloxycarbonylation, a rhodium catalyzed asymmetric hydroformylation and a magnesium enolate addition reaction as the key reaction, respectively.
Databáze:	OpenAIRE
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