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US 6,555,686 B2Granted
Asymmetric synthesis of quinazolin-2-ones useful as HIV reverse transcriptase inhibitors
AssigneeBristol-Myers Squibb Pharma Company
InventorsRodney L. Parsons, Roberta L. Dorow, Akin H. Davulcu, Joseph M. Fortunak, Gregory D. Harris, Goss S. Kauffman, William A. Nugent, Lilian A. Radesca
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Abstract
This invention relates generally to the asymmetric synthesis of quinazolin-2-ones that are useful as inhibitors of HIV reverse transcriptase. The synthesis is accomplished through the chiral ligand mediated addition of cyclopropylacetylide.
Claims44
A process for making a compound of Formula Ia or Formula Ib:
- comprising:
- contacting a quinazolinone precursor of Formula IIa or IIb:
- with cyclopropylacetylene in the presence of a chiral moderator and a base, wherein the chiral moderator is a compound selected from:
A process for making a compound of Formula Ia or Formula Ib:
- comprising:
- contacting a quinazolinone precursor of Formula IIa or IIb:
- with cyclopropylacetylene in the presence of a chiral moderator and a base, wherein the chiral moderator is a compound that provides an enantiomeric excess of at least 30 to 100%.
Dependencies are inferred from the claim text.