Bulletin of the Korean Chemical Society

  • 제13권3호
  • /
  • Pages.311-314
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  • 1992
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Total Synthesis of Sodium (3R,4S)-3-[2-(2-Aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-4-methoxymethyl-2-azetidinone-1-sulfonate from L-Aspartic Acid

  • 발행 : 1992.06.20
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초록

A new monocyclic ${\beta}-lactam$ analogue, sodium (3R,4S)-3-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyi minoacetamido]-4-methoxymethyl-2-azetidinone-1- sulfonate (3) was synthesized from L-aspartic acid. Starting from L-aspartic acid, (S)-1-benzyl-4-benzyloxycarbonyl-2-azetidinone (7) was synthesized in four steps by following the established procedures and converted into (3R,4S)-3-amino-1-t-butyldimethylsilyl-4-methoxym ethyl-2-azetidinone (13) in six steps. Acylation of the amino group of 13 with $2-amino-{\alpha}$ -(methoxyimino)-4-thiazoleacetic acid, desilylation, and sulfonation with sulfur trioxide-pyridine complex followed by ion exchange afforded sodium (3R,4S)-3-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyi minoacetamido]-4-methoxymethyl-2-azetidinone-1- sulfonate (3). Antibacterial activities of this ${\beta}$ -lactam compound 3 were, however, found to be quite low compared to cefotaxime.

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