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85033864531
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note
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Model studies have demonstrated the tandem sequence of alkylation, cyclization (with liberation of LiOBn), and butyl ester cleavage ensues as the temperature rises above ca. 15 °C.
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38
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0000328128
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Glycidyl Ether Reactions with Urethanes and Ureas. A New Synthetic Method for 2-Oxazolidones
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Prior use of urethanes and epoxides to synthesize 3-alkyl- or 3-unsubstituted oxazolidinones are known, for example, reactions run neat, catalyzed by (a) tertiary amines: Iwakura, Y.; Izawa, S.-I. Glycidyl Ether Reactions with Urethanes and Ureas. A New Synthetic Method for 2-Oxazolidones. J. Org. Chem. 1964, 29, 379. (b) Lithium amide: Markley, F. X.; Horton, R. L.; Weinberger, K. A. 5-Aryloxymethyl-2-oxazolidinones. French Patent Addn. 80,105, March 22, 1963; Chem. Abstr. 1963, 59, 10058.
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5-Aryloxymethyl-2-oxazolidinones. French Patent Addn. 80,105, March 22, 1963
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Prior use of urethanes and epoxides to synthesize 3-alkyl- or 3-unsubstituted oxazolidinones are known, for example, reactions run neat, catalyzed by (a) tertiary amines: Iwakura, Y.; Izawa, S.-I. Glycidyl Ether Reactions with Urethanes and Ureas. A New Synthetic Method for 2-Oxazolidones. J. Org. Chem. 1964, 29, 379. (b) Lithium amide: Markley, F. X.; Horton, R. L.; Weinberger, K. A. 5-Aryloxymethyl-2-oxazolidinones. French Patent Addn. 80,105, March 22, 1963; Chem. Abstr. 1963, 59, 10058.
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85033849065
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note
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Enantiomeric purity levels were determined using a Chiralcel OJ column (Daicel Chemical Industries, Ltd., Tokyo).
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41
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0037882741
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In Vitro Antibacterial Activity of U-100592 and U-100766, Novel Oxazolidinone Antibiotics
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San Francisco, CA, Abstract F216
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Zurenko, G.E.1
Yagi, B.H.2
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Brickner, S.J.7
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42
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0002689090
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Synthesis of U-100592 and U-100766, Two New Oxazolidinone Antibacterial Agents in Clinical Trials for Treatment of Multiply Resistant Gram Positive Infections
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San Francisco, CA, Abstract F208
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Brickner, S. J.; Hutchinson, D. K.; Barbachyn, M. R.; Garmon, S. A.; Grega, K. C.; Hendges, S. K.; Manninen, P. R.; Toops, D. S.; Ulanowicz, D. A.; Kilburn, J. O.; Glickman, S. E.; Zurenko, G. E.; Ford, C. W. Synthesis of U-100592 and U-100766, Two New Oxazolidinone Antibacterial Agents in Clinical Trials for Treatment of Multiply Resistant Gram Positive Infections. 35th Interscience Conference on Antimicrobial Agents and Chemotherapy, San Francisco, CA, 1995; Abstract F208.
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Brickner, S.J.1
Hutchinson, D.K.2
Barbachyn, M.R.3
Garmon, S.A.4
Grega, K.C.5
Hendges, S.K.6
Manninen, P.R.7
Toops, D.S.8
Ulanowicz, D.A.9
Kilburn, J.O.10
Glickman, S.E.11
Zurenko, G.E.12
Ford, C.W.13
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43
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9244240601
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San Francisco, CA, Abstract F222
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Martin, I.J.1
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44
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0007357058
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Drug Safety Evaluation of U-100592, an Oxazolidinone Antibiotic, in Dogs and Rats
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San Francisco, CA, Abstract F223
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(a) Piper, R. C.; Lund, J. E.; Denlinger, R. H.; Platte, T. F.; Brown, W. P.; Brown, P. K.; Palmer, J. R. Drug Safety Evaluation of U-100592, an Oxazolidinone Antibiotic, In Dogs and Rats. 35th Interscience Conference on Antimicrobial Agents and Chemotherapy, San Francisco, CA, 1995; Abstract F223.
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(1995)
35th Interscience Conference on Antimicrobial Agents and Chemotherapy
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Piper, R.C.1
Lund, J.E.2
Denlinger, R.H.3
Platte, T.F.4
Brown, W.P.5
Brown, P.K.6
Palmer, J.R.7
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45
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0344120546
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Drug Safety Studies with a Novel Oxazolidinone, U-100766
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San Francisco, CA, Abstract F224
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(b) Koike, S.; Miura, H.; Nakamura, R.; Chiba K.; Moe, J. B. Drug Safety Studies with a Novel Oxazolidinone, U-100766. 35th Interscience Conference on Antimicrobial Agents and Chemotherapy, San Francisco, CA, 1995; Abstract F224.
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(1995)
35th Interscience Conference on Antimicrobial Agents and Chemotherapy
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Koike, S.1
Miura, H.2
Nakamura, R.3
Chiba, K.4
Moe, J.B.5
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