Sulfilimine and sulphoxide methods for producing festinavir

摘要

A process for making the compound of Formula I utilizes the starting compound, together with sulfilimine and sulfoxide process steps later on.;

主权项

1. A process for making the compound of Formula I which comprises: (1a) contacting the starting compoundwith p-thiocresol and N,N-diisopropylethylamine (DIPEA) to produce the compound 1aand
(1b) contacting the compound 1a with the trimethylsilylation (TMS) reagent TMS-Li-acetylide in solution to yield the compound 1band
(2) contacting the compound 1b with aqueous HCl in acetonitrile (MeCN), followed by reaction with benzoic anhydride and 4-dimethylamino pyridine (DMAP), and then reaction with aqueous K3PO4 in dimethylformamide (DMF) to yield the compound 2and
(3) contacting the compound 2 with the compound N,N-Bis-TMS-thymineto produce the compound 3and
(4a) contacting the compound 3 with chloramine-T or phenyliodine (bis)trifluoroacetate (PIFA) to produce the compound 4awherein X=O or NTs; and
(4b) contacting the compound 4a with dimethylsulfoxide (DMSO) or n-butyl alcohol (n-BuOH), and heating to produce the compound 4band
(5) contacting the compound 4b with 1,8-diazabicycloundec-7-ene (DBU) and MeOH, or NaOH in THF, for benzoate ester hydrolysis to yield the compound of Formula I.