Methods of making efavirenz and intermediates thereof

Details Methods of making efavirenz and intermediates thereof Methods of making efavirenz and intermediates thereof

2009-07-20

2011-12-20

Wilson, James O (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Chalcogen in the nitrogen containing substituent

Reexamination Certificate

active

08080655

ABSTRACT:
The present invention provides a process for the preparation of Efavirenz. A compound of Formula 1:may be prepared by a process comprising cyclizing, in the presence of a first base, a compound of Formula 5 with a haloformate of Formula 6. Other processes are also provided as well as novel compounds prepared by and used in such processes.

REFERENCES:
Chen et al., “Chemical Process Evolution of Efavirenz, a Potent Non-Nucleosidal HIV Reverse Transcriptase Inhibitor”, Enantiomer, (1999), 4(6), 599-608.
Choudhury et al., “In Situ Recycling of Chrial Ligand and Surplus Nucleophile for a Noncatalytic Reaction: Amplification of Process Throughput in the Asymmetric Addition Step of Efavirens (DMP 266)”, Organic Process Research & Development, (2003), 7(3), 324-328.
Choudhury et al., “Oxidative Removal of p-methyl-oxybenzyl-amino Protecting Group in the Presence of a Proximal Hydroxy Function: A Solution to a Process Problem in Sustiva(R) (Efavirenz) Synthesis”, Synthetic Communications, (2001), 31(23), 3707-3714.
Jiang et al., “alpha-(Trifluoromethyl)ethenyl Boronic Acid as a Useful Trifluoromethyl Containing Building Block. Preparation and Palladium-Catalysed Coupling with Aryl Halides”, Tetrahedron Letters, (2001), 42(24), 4083-4085.
Markwalder et al., “Synthesis and Biological Activities of Protential Metabolites of the Non-Nucleoside Reverse Transcriptase Inhibitor Efavirenz”, Bioorganic & Medicinal Chemistry Letters, (2001), 11(5), 619-622.
Pedersen et al., “The Flourishing Synthesis of Non-Nucleoside Reverse Transcriptase Inhibitors”, Synthesis, (2000), (4), 479-495.
Radesca et al., “Synthesis of HIV-1 Reverse Transcriptase Inhibitor DMP 266”, Synthetic Communications, (1997), 27(24), 4373-4384.

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