7-Aminocephalosporanic acid를 포함하는 Aminophosphonate유도체의 합성

김상범

Journal of the Korean Industrial and Engineering Chemistry, Vol.8, No.4, 700-703, August, 1997

Export Citation

7-Aminocephalosporanic acid를 포함하는 Aminophosphonate유도체의 합성

Synthesis of Aminophosphonate Derivatives Containing 7-Aminocephalosporanic acid

김상범

초록

Phthalic anhydride를 출발물질로 halogenation, phosphorylation하여 diethyl phthalimidoalkylphosphonate를 합성하였다. 이 화합물을 chlorination하여 O-ethyl phthalimidoalkylphosphonate을 만든후 diphenylmethyl 7-β-amino-3-acetoxymethyl-3-cephem-4-carboxylate와 coupling하여 지금까지 알려져 있지 않은 화합물 diphenylmethyl-7-β-(O-ethylphthalimidomethylphosphony1)-3-acetoxymethyl-3-cephem-4-carboxylate와 diphenylmethyl-7-β-[O-ethylphthalimidoethylphosphonyl]-3-acetoxymethyl-3-cephem-4-carboxylate를 각각 19%, 43%의 수율로 합성하였다.

7-Aminocephalosporanic acid(7-ACA) was reacted with diphenyldiazomethane(DPM) to get diphenylmethyl 7-β-(O-ethylphthalimidomethylphosphony1)-3-acetoxymethyl-3-cephem-4-carboxylate. Diethyl phthalimidomethylphosphonate was chloridated with a slight excess of phosphorus pentachloride to the O-ethyl phthalimidoalkylphosphonochloridate. Previously unreported two compounds, diphenylmethy1 -7-β-(O-ethylphthalimidomethylphosphony1)-3-acetoxymethyl-3-cephem-4-carboxylate and diphenylmethyl-7-β-[O-ethylphthalimidoethylphosphonyl]-3-acetoxymethyl-3-cephem-4-carboxylate were synthesized by cupling reaction of DPM 7-ACA and O-ethyl phthalimidoalkylphosphonochloridate. All of the compounds including starting materials and reaction intermediates were characterized by ¹H NMR and FT-IR spectroscopy.

[References]

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[1] Horiguchi M, Kandatsu M, Nature, 184, 901 (1959)

[2] Alhadeff JA, Davies GD, J. Biochem., 9, 4866 (1970)

[3] Hoigychi M, Biochem. Biophys. Acta, 261, 102 (1967)

[4] Bioulac B, Gen. Pharmaceu., 10, 121 (1979)

[5] Tamari H, Horiguchi M, Kandatsu M, J. Gen. Appl. Microbiol., 23, 49 (1977)

[6] Kim SB, Kim YJ, Hong SI, J. Korean Chem. Soc., 38, 682 (1994)

[7] Quin, Science, 144, 1133 (1964)

[8] Okada Y, Iguchi S, Mimura M, Yagyu M, Chem. Pharm. Bull., 28, 1320 (1980)

[9] Lejczak B, Kafarski P, Sztajer H, Mastalertz P, J. Med. Chem., 29, 2212 (1986)

[10] Takaya T, Chiba T, Jpn. Kokai Tokyo Kaho Japan Patent, 55-115, 892 (1980)

[11] Campbell MM, Carruthers NI, Mickle SJ, Tetrahedron, 38, 2513 (1982)

[12] Satoh H, Tsuji T, Tetrahedron Lett., 25, 1733 (1984)

[13] Soine TD, Org. Synth. Coll., 4, 106 (1967)

[14] Nefkens HHL, Nature, 193, 974 (1962)

[15] Yamauchi K, Ohtsuki S, Kinoshita M, Bull. Chem. Soc. Jpn., 49, 1158 (1984)

[16] Yamauchi K, Kinoshita M, Imoto M, Bull. Chem. Soc. Jpn., 45, 2531 (1972)

[17] Kosolapoff GM, J. Am. Chem. Soc., 66, 109 (1944)

[18] Micetich RG, Singh R, Synthesis, 693 (1985)