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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 10
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Original Articles

Improved Synthesis of Amino Acid and Dipeptide Chloromethyl Esters Using Bromochloromethane

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Pages 1683-1693 | Received 14 May 2002, Published online: 17 Aug 2006

References

  • Korolkovas , A. 1988 . Essentials of Medicinal Chemistry, , 2nd Ed. New York : John Wiley & Sons .
  • Julien , R.M. 1987 . Drugs and the Body Edited by: Atkinson , R.C. , Lindzey , G. and Thompson , R.F. New York : W. H. Freeman & Co. .
  • Hughes , R.A. , Toth , I. , Ward , P. , McColm , A.M. , Cox , D.M. , Andersson , G.J. and Gibbons , W.A. 1992 . Lipidic peptides. 5. Penicillin and cephalosporin acid conjugates with increased lipophilic character . J. Pharm. Sci. , 81 ( 8 ) : 845 – 848 .
  • Lopes , F. , Moreira , R. and Iley , J. 1999 . Acyloxymethyl as a drug protecting group. Part 5: kinetics and mechanism of the hydroslysis of tertiary N-acyloxmethylsulfonamides . J. Chem. Soc., Perkin Trans. 2 , : 431 – 439 .
  • Lopes , F. , Moreira , R. and Iley , J. 2000 . Acyloxymethyl as a drug protecting group. Part 6: N-acyloxymethyl- and N-[(aminocarbonyloxy)methyl]sulfonamides as prodrugs of agents containing a secondary sulfonamide group . Bioorg. Med. Chem. , 8 : 707 – 716 .
  • Iley , J. , Barroso , H. , Moreira , R. , Lopes , F. and Calheiros , T. 2000 . Acyloxymethyl as a drug protecting group. Part 7: tertiary sulfonamidomethyl ester prodrugs of benzylpenicillin: chemical hydrolysis and anti-bacterial activity . Bioorg. Med. Chem. , 8 : 1629 – 1636 .
  • Wheeler , W.J. , Preston , D.A. , Wright , W.E. , Huffman , G.W. , Osborne , H.E. and Howard , D.P. 1979 . Orally active esters of cephalosporin antibiotics. 3. Synthesis and biological properties of aminoacyloxymethyl esters of 7-[d-(−)-mandelamido]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-3-cephem-4-carboxylic acid . J. Med. Chem. , 22 : 657 – 661 .
  • Harada , N. , Hongu , M. , Tanaka , T. , Kawaguchi , T. , Hashiyama , T. and Tsujihara , K. 1994 . A simple preparation of chloromethyl esters of the blocked amino acids . Synth. Comm. , 24 ( 6 ) : 767 – 778 .
  • Binderup , E. and Hansen , E.T. 1984 . Chlorosulfates as reagents in the synthesis of carboxylic acid esters under phase-transfer conditions . Synth. Comm. , 14 ( 9 ) : 857 – 864 .
  • Gisin , B.F. 1973 . The preparation of Merrifield-Resins through total esterification with cesium salts . Helv. Chim. Acta , 56 ( 5 ) : 1476 – 1482 .
  • Martínez , J. , Laur , J. and Castro , B. 1983 . Carboxamidomethyl esters (CAM esters) as carboxyl protecting groups . Tetrahedron Lett. , 24 ( 47 ) : 5219 – 5222 .
  • Biochemistry Nomenclature Committee of the IUPAC-IUB (specified in Eur . J. Biochem. 1984, 138, 9 and in J. Biol. Chem. 1989, 264, 633)

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