ChemInform Abstract: THE SYNTHESIS OF D,L‐CIS‐N‐OXALAMIDO‐3‐N‐PHENYLACETAMIDO‐4‐METHOXYMETHYL‐2‐AZETIDINONE

Just, George; Liak, T. J.

doi:10.1002/chin.197822156

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“…We treated racemic azetidione acrylic acid 5 14 with benzyl bromide and K 2 CO 3 in DMF to produce the corresponding benzyl ester 6 in 90% yield. Acrylate 6 and fumarate 7 15 were converted to the corresponding diastereoisomeric phosphonates 8 (95% yield) and 9 (80% yield), respectively, using diphenyl phosphite and a catalytic amount of NaH in THF.…”

Section: Synthesis Of Carbapenems (()-21 and (()-22 (Scheme 1)mentioning

confidence: 99%

Design, Synthesis, and SAR of Novel Carbapenem Antibiotics with High Stability to Xanthomonas maltophilia Oxyiminocephalosporinase Type II

et al. 2000

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Racemic cis-6-(phenylacetamido)carbapenem (21), 2-hydroxycarbonyl-cis-6-(phenylacetamido)carbapenem (22), 2-methoxycarbonyl-cis-6-(phenylacetamido)carbapenem (30), 2-methoxycarbomethyl-cis-6-(phenylacetamido)carbapenem (33), 2-hydroxyethyl-cis-6-(phenylacetamido)carbapenem (34), and 2-acetoxyethyl-cis-6-(phenylacetamido)carbapenem (35) were synthesized. Formation of the carbapenem nuclei in 21, 22, and 30 involved dehydrophosphonation of the corresponding 2-diphenylphosphono-6-(phenylacetamido)carbapenam precursors 14, 15, and 28 using trimethylsilyl triflate and 1,8-diazabicyclo[5.4.0]undec-7-ene in THF. Syntheses of carbapenems 33-35 involved a Wittig reaction of carbapenam 14 with methyl glyoxylate in the presence of lithium 2,2,6,6-tetramethylpiperidine in THF. For the antibacterial activities against Staphylococcus aureus FDA 209P, S. aureus 95, Escherichia coli ATCC 39188, Klebsiellapneumoniae NCTC 418, Pseudomonas aeruginosa 1101-75, and P. aeruginosa 18S-H, carbapenems (+/-)-21, (+/-)-22, (+/-)-30, and (+/-)-33-35 were found comparable with imipenem ((+)-3), yet they were notably more potent than (+)-3 against Xanthomonas maltophilia GN 12873. On the other hand, unlike (+)-3, carbapenems (+/-)-21, (+/-)-22, (+/-)-30, and (+/-)-33-35 were stable to X. maltophilia oxyiminocephalosporinase type II. Their beta-lactamase inhibitory properties, however, were found to be more comparable with those of penicillin G ((+)-4) than to those of imipenem ((+)-3). A combination of imipenem ((+)-3) with (+/-)-21, (+/-)-22, (+/-)-30, and (+/-)-33-35 resulted in synergistic antibacterial activity against X. maltophilia GN 12873. Results from the biological tests were correlated with the distribution of the electron density at C(2)=C(3) of carbapenems upon reaction with transpeptidases or beta-lactamases.

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Section: Synthesis Of Carbapenems (()-21 and (()-22 (Scheme 1)mentioning

confidence: 99%

Design, Synthesis, and SAR of Novel Carbapenem Antibiotics with High Stability to Xanthomonas maltophilia Oxyiminocephalosporinase Type II

et al. 2000

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ChemInform Abstract: THE SYNTHESIS OF D,L‐CIS‐N‐OXALAMIDO‐3‐N‐PHENYLACETAMIDO‐4‐METHOXYMETHYL‐2‐AZETIDINONE

Abstract: Ausgehend vom L‐Serin (Ia) wird über die Silylverbindung (Ib) nach angegebenem Schema die Titelverbindung (VII) in 18proz. Ausb. erhalten.

Cited by 1 publication

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Design, Synthesis, and SAR of Novel Carbapenem Antibiotics with High Stability to Xanthomonas maltophilia Oxyiminocephalosporinase Type II

Design, Synthesis, and SAR of Novel Carbapenem Antibiotics with High Stability to Xanthomonas maltophilia Oxyiminocephalosporinase Type II

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