Aerobic Oxidation of 3-Iodomethyl-Δ3-cephem-4-carboxylate to 3-Formyl-Δ3-cephem-4-carboxylate through 3-Hydroperoxymethyl-Δ3-cephem-4-carboxylate

Hideo Tanaka, Ryo Kikuchi, Sigeru Torii

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Abstract

Aerobic oxidation of p-methoxybenzyl 3-iodomethyl-8-oxo-7-phenylacetamido-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2- carboxylate (3-iodomethyl-7-phenylacetamido-Δ3-cephem-4-carboxylate) in N-methyl-2-pyrrolidone in the presence of phosphomolybdic acid mainly afforded the corresponding 3-formyl-Δ3-cephem-4-carboxylate, while similar aerobic oxidation in the presence of potassium iodide gave 3-hydroxymethyl-Δ3-cephem-4-carboxylate as a major product. 3-Hydroperoxymethyl-Δ3-cephem-4-carboxylate was isolated as a primary product in the aerobic oxidation, which was subsequently converted to either 3-formyl-Δ3-cephem-4-carboxylate by dehydration with phosphomolybdic acid or 3-hydroxymethyl-Δ3-cephem-4-carboxylate by reduction with potassium iodide.

Original languageEnglish
Pages (from-to)229-233
Number of pages5
JournalBulletin of the Chemical Society of Japan
Volume69
Issue number1
Publication statusPublished - Jan 1996

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Potassium Iodide
Oxidation
Dehydration
phosphomolybdic acid
N-methylpyrrolidone

ASJC Scopus subject areas

  • Chemistry(all)

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Aerobic Oxidation of 3-Iodomethyl-Δ3-cephem-4-carboxylate to 3-Formyl-Δ3-cephem-4-carboxylate through 3-Hydroperoxymethyl-Δ3-cephem-4-carboxylate. / Tanaka, Hideo; Kikuchi, Ryo; Torii, Sigeru.

In: Bulletin of the Chemical Society of Japan, Vol. 69, No. 1, 01.1996, p. 229-233.

Research output: Contribution to journalArticle

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abstract = "Aerobic oxidation of p-methoxybenzyl 3-iodomethyl-8-oxo-7-phenylacetamido-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2- carboxylate (3-iodomethyl-7-phenylacetamido-Δ3-cephem-4-carboxylate) in N-methyl-2-pyrrolidone in the presence of phosphomolybdic acid mainly afforded the corresponding 3-formyl-Δ3-cephem-4-carboxylate, while similar aerobic oxidation in the presence of potassium iodide gave 3-hydroxymethyl-Δ3-cephem-4-carboxylate as a major product. 3-Hydroperoxymethyl-Δ3-cephem-4-carboxylate was isolated as a primary product in the aerobic oxidation, which was subsequently converted to either 3-formyl-Δ3-cephem-4-carboxylate by dehydration with phosphomolybdic acid or 3-hydroxymethyl-Δ3-cephem-4-carboxylate by reduction with potassium iodide.",
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