2315-05-1

Basic information

• Product Name: 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-(phenoxyacetamido)-, methyl ester
• Synonyms: methyl 6-phenoxyacetamido-2,2-dimethylpenam-3-carboxylate;methyl phenoxymethylpenicillinate;phenoxymethylpenicillin methyl ester;Penicillin-V methylester
• CAS NO: 2315-05-1
• Molecular Formula: C17H20N2O5S
• Molecular Weight: 364.422
• Mol File: 2315-05-1.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-(phenoxyacetamido)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-(phenoxyacetamido)-, methyl ester(2315-05-1)
• EPA Substance Registry System: 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-(phenoxyacetamido)-, methyl ester(2315-05-1)

Safety Data

• Hazardous Substances Data: 2315-05-1(Hazardous Substances Data)

Upstream product

• 87-08-1 penicilin V 
• 158411-82-6 (+/-)-N-formylpenicillamine 
• 58134-39-7 methyl 5,5-dimethyl-2-thiazoline-4-carboxylate 
• 701-99-5 Phenoxyacetyl chloride 
• 551-16-6 6-Aminopenicillanic Acid 
• 132-98-9 penicillin V potassium 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 186581-53-3 diazomethane 
• 37628-54-9 6β-benzylideneamino-penicillanic acid methyl ester 

Downstream Products

• 56671-55-7 3-methyl-2-[((E)-2-phenoxymethyl-5-thioxo-oxazol-4-ylidenemethyl)-amino]-but-2-enoic acid methyl ester 
• 56671-56-8 4-((E)-cyclohexylamino-methylene)-2-phenoxymethyl-4H-oxazole-5-thione 
• 56671-54-6 6α-(1-chloro-2-phenoxy-ethylideneamino)-penicillanic acid methyl ester 
• 95777-20-1 (S)-2-[2-Bromo-1-(2-phenoxy-acetylamino)-ethyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid methyl ester 
• 95519-41-8 methyl 5,5-dimethyl-2-(2-phenoxy-4,5-dihydro-1,3-oxazol-4-yl)thiazolidine-4-carboxylate 
• 87616-44-2 2-{(R)-2-Chloro-3-[2-(4-chloro-phenoxy)-acetylamino]-4-oxo-azetidin-1-yl}-3-methyl-but-2-enoic acid methyl ester 
• 1243-65-8 (S)-2-[2-Hydroxy-1-(2-phenoxy-acetylamino)-ethyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid methyl ester 
• 52512-73-9 3-methyl-2-((1S)-7-oxo-3-phenoxymethyl-(1rH,5cH)-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-2-enoic acid methyl ester 
• 19707-45-0 (R)-α-[(S)-2-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-isovaleric acid methyl ester 
• 41625-63-2 methyl phenoxymethylpenicillinate 1,1-dioxide 
• 25547-92-6 1α-oxo-6β-(2-phenoxy-acetylamino)-1λ⁴-penicillanic acid methyl ester 
• 10209-03-7 methyl 6β-phenoxyacetamidopenicillanate-1β-sulfoxide 
• 56671-53-5 6β-(1-chloro-2-phenoxy-ethylideneamino)-penicillanic acid methyl ester 
• 61139-39-7 6α-ethoxycarbonylamino-6β-(2-phenoxy-acetylamino)-penicillanic acid methyl ester 

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Synthesis and decarboxylation of Δ2-cephem-4,4-dicarboxylic acids

Penicillin V was converted in 14 steps into Δ2-cephems having hydrogen at C-3, hydrogen or methyl at C-2, and two methoxycarbonyl, two benzyloxycarbonyl, or one methoxycarbonyl and one benzyloxycarbonyl substituent at C-4. Deprotection of these Δ2-cephem-4,4-dicarboxylic acid esters by alkaline hydrolysis (in the case of methyl esters) or hydrogenolysis (in the case of benzyl esters) led in all cases to rapid decarboxylation of the Δ2-cephem-4,4-dicarboxylic acid or Δ2-cephem-4,4-dicarboxylic acid monoester. With hydrogen at C-2, hydrolysis of the dimethyl ester with 1 equiv of base produced a Δ2-cephem. With 2 equiv of base, and with all compounds having methyl at C-2, hydrolysis or hydrogenolysis afforded 4α-substituted-Δ2-cephems. In contrast, simpler benzyl or methyl acetamidomalonates could be deprotected without difficulty to afford stable malonic acids. Reasons for the differences in ease of decarboxylation were examined using semiempirical (AM1) and ab initio (3-21G) molecular orbital calculations. The decarboxylation barriers of unionized cephem or acetamido malonic acids were found to be high (35-40 kcal mol-1). Although the monoanion of acetamidomalonic acid retained a high barrier, the epimeric monoanions of a Δ2-cephem malonic acid decarboxylated with barriers of only 2 kcal mol-1.