99147-22-5

Upstream product

• 69-96-5 dl-threo-phenylserine 
• 501-53-1 benzyl chloroformate 
• 69-96-5 (2RS,3RS)-2-amino-3-hydroxy-3-phenyl-propionic acid 
• 78498-83-6 (3RS)-7-chloro-1,3-dihydro-3-[(1SR)-hydroxy(phenyl)methyl]-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one 

Downstream Products

• 7705-78-4 (1-hydrazinocarbonyl-2-hydroxy-2-phenyl-ethyl)-carbamic acid benzyl ester 
• 103642-46-2 (2RS,3SR)-2-benzyloxycarbonylamino-3-hydroxy-3-phenyl-propionic acid benzyloxyamide 
• 93847-72-4 ((1S,2R)-2-Hydroxy-2-phenyl-1-p-tolylcarbamoyl-ethyl)-carbamic acid benzyl ester 
• 93847-79-1 ((3R,4R)-2-Oxo-4-phenyl-1-p-tolyl-azetidin-3-yl)-carbamic acid benzyl ester 
• 93847-83-7 cis-1-carbobenzyloxy-2-phenyl-3-(N-p-tolyl)amidoaziridine 
• 74805-42-8 N-carboxy-α-dehydrophenylalanine anhydride 
• 72015-61-3 (Z)-2-benzyloxycarbonylaminocinnamic acid 
• 74805-50-8 (Z)-4-benzylideneoxazolidine-2-one 
• 74805-57-5 (Z)-1-hydroxy-4-benzylideneimidazolidine-2,5-dione 
• 74805-59-7 (Z)-1-phenyl-4-benzylideneimidazolidine-2,5-dione 
• 74805-54-2 (Z)-5-benzylidene-2-phenyl-as-triazine-3,6-dione 
• 74805-56-4 N-benzyloxycarbonyl-(Z)-dehydrophenylalanine hydroxamic acid 
• 74805-62-2 N-benzyloxycarbonylbenzylcarboximidic acid isopropyl ester 
• 74805-49-5 (Z)-1,1-diethyl-(2-benzyloxycarbonylamino)cinnamyl alcohol 

Relevant academic research and scientific papers

syn/anti Diastereoselectivity in the aldol reaction of aldehydes with the C(3) carbanion of 1,3-dihydro-2H-1,4-benzodiazepin-2-one

The aldol reaction of the C(3) carbanion of 7-chloro-1,3-dihydro-1- methyl-5-phenyl-2H-1,4-benzodiazepin-2-one (2) with a series of aromatic and aliphatic aldehydes at -78°afforded threo/erythro diastereoisomers 3-16 of 7-chloro-1,3-dihydro-3-(hydroxymethyl)-1-methyl-5-phenyl-2H-1,4- benzodiazepinones, substituted at the C(3) side chain, in a ratio from 55:45 to 94:6 (Scheme 1). Lewis acids exhibited limited effect on the syn/anti diastereoselectivity of this reaction, and kinetic control of the reaction was confirmed. 1H-NMR Data suggested the assignment of the threo relative configuration to the first-eluted diastereoisomers 3, 5 7, and 9 on reversed- phase HPLC, and the erythro configuration to the second-eluted counterparts 4, 6, 8, and 10, respectively. The structures and relative configurations threo and erythro of the diastereoisomers 5 and 6, respectively, were established by single-crystal X-ray analysis, confirming the assignment based on the 1H-NMR data. A tentative mechanistic explanation of the diastereoselectivity invokes the enolate anion of 1,3-dihydro-2H-1,4- benzodiazepin-2-one as the reactive species (Scheme 2). Acid-catalyzed hydrolytic ring opening of 3 afforded threo-β-hydroxy-phenylalanine 17, whereas from 4, the N-(benzyloxy)carbonyl derivative 18 of erythro-β- hydroxy-phenylalanine was obtained (Scheme 3); in both cases, neither elimination of H2O from the C(3)-CHOH moiety nor epimerization at C(3) were observed. This result opens a new pathway to various configurationally uniform α-amino-β-hydroxy carboxylic acids and their congeners of biological importance.

Composition containing a penem or carbapenem antibiotic and the use of the same

Administration of an N-acylated amino acid in association with a penem or carbapenem antibiotic relieves or eliminates the renal problems associated with administration of the antibiotic alone. The amino acid derivative and antibiotic may be formulated together as a composition or administered separately, either simultaneously or sequentially.

Composition containing a penem or carbapenem antibiotic

Administration of an N-acylated amino acid in association with a penem or carbapenem antibiotic relieves or eliminates the renal problems associated with administration of the antibiotic alone. The amino acid derivative and antibiotic may be formulated together as a composition or administered separately, either simultaneously or sequentially. The composition may be prepared by simple mixing.