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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 23
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Original Articles

OXIDATIVE REMOVAL OF p-METH-OXYBENZYL-AMINO PROTECTING GROUP IN THE PRESENCE OF A PROXIMAL HYDROXY FUNCTION: A SOLUTION TO A PROCESS PROBLEM IN SUSTIVA® (EFAVIRENZ) SYNTHESIS

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Pages 3707-3714 | Received 07 Feb 2001, Published online: 16 Aug 2006

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  • The oximation reaction was very slow in toluene but could be facilitated by addition of alcohols like ethanol or 1-propanol. Although amino alcohol 4 could be isolated by solvent exchanging the reaction mixture with heptane, the product sometimes was contaminated with oxime and the result was not reproducible. Removal of anisaldehyde oxime as its sodium salt by addition of aq. NaOH resulted in partial reversion to the hemiaminal. Analytical HPLC were run with Zobrax RX-C18 columns at 215, 240, and 250 nm
  • The product was identical in all aspects with that previously reported (Ref. [5])

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