An efficient synthesis of N-hydroxy-N'-[4-3H]phenyloctanediamide ([4-3H]SAHA), a potent cytodifferentiating agent

Dhimant Desai, Victor Sidorov, Joseph Backer, Shantu Amin

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Abstract

We have developed an efficient synthesis of N-hydroxy-N'-[4-3H]phenyloctanediamide ([4-3H]SAHA) from the monoester of suberanilic acid. The starting material, a monoester of suberoyl chloride, was condensed with 4-bromoaniline in the presence of a base to give the 4-bromoanilide of monoethyl suberate in 92% yield. On further treatment with methanolic hydroxylamine hydrochloride and sodium methoxide, this compound gave 4-bromosuberanilohydroxamic acid in 94% yield. Catalytic tritium exchange of bromine using Pd/C in a tritium gas atmosphere resulted in [4-3H]SAHA with a specific activity of 2.49 Ci/mmol. From the key intermediate, 4-bromoanilide of monoethyl suberate by a non-catalytic tritium exchange reaction, we have also prepared [4-3H]SAHA with high specific activity of 27.5 Ci/mmol.

Original languageEnglish (US)
Pages (from-to)229-236
Number of pages8
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume43
Issue number3
DOIs
Publication statusPublished - Mar 15 2000

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All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Radiology Nuclear Medicine and imaging
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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