Process for indinavir intermediate

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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C07D26352

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active

059817593

ABSTRACT:
An intermediate in the synthesis of indinavir is prepared by iodohydroxylating an allyl acetonide by hypoiodous acid generated in situ from sodium hypochlorite and sodium iodide. ##STR1##

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K. Rossen et al., "Asymmetric Hydrogenation of Tetrahydropyrazines: Synthesis of (S)-Piperazine-2-tert-butylcarboxamide, and Intermediate in the Preparation of the HIV Protease Inhibitor indinavir", Tetrahedron Letters, vol. 36, No. 36, pp. 6419-6422 (1995).
D. Askin et al., "Highly Diastereoselective Reaction of a Chiral, Non-Racemic Amide Enolate with (S)-Glycidyl Tosylate. Synthesis of the Orally Active HIV-1 Protease Inhibitor L-735,524", Tetrahedron Letters, vol. 35, No. 5, pp. 673-676 (1994).
P. E. Maligres et al., "Diastereoselective Syn-Epoxidation of 2-Alkyl-4-Enamides to Expoxyamides: Synthesis of the Merck HIV-1 Protease Inhibitor Epoxide Intermediate", Tetrahedron Letters, vol. 36, No. 13, pp. 2195-2198 (1995).
Rossen et al., "Mechanistic Studies on the Diastereoselective Halohydroxylation of Gamma-Delta Unsaturated Carboxamides", Tetrahedron Letters, vol. 37, No. 38, pp. 6843-6846 (1996).
P. E. Maligres et al., "Cyclic Imidate Salts in Acyclic Stereochemistry: Diastereoselective Syn-Expoxidation of 2-Alkyl-4-Enamides to Epoxyamides", Tetrahedron Letters, vol. 52, No. 9, pp. 3327-3338 (1996).
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