Tert-butyl sulphoxide method for producing festinavir

Patent metadata

Field	Value
Publication number	US-2016130260-A1
Application number	US-201414896995-A
Country	US
Kind code	A1
Filing date	Jun 11, 2014
Priority date	Jun 13, 2013
Publication date	May 12, 2016
Grant date	—

Abstract

Tert-butyl sulphoxide method for producing festinavir is set forth.

First claim

What is claimed is:

1 . A process for making the compound of Formula I

which comprises:
(1) contacting the starting compound (S)—S-tert-butyl 2-methylpropane-2-sulfinothioate with the Grignard reagent generated from 3-bromo-1,1-dimethoxypropane to produce

compound 1a.

and then contacting compound 1a with p-thiocresol and BF 3 -Et 2 O to produce the compound 1b

and
(2) contacting compound 1b with n-BuLi and compound 2

to produce the compound 3, after removal of the silicon groups with TBAF and then re-protection of the C-5 hydroxy group as its benzoate ester (4-DMAP, Bz 2 O)

and
(3) contacting the compound 3 with Bis-TMS-thymine

and NBS in nitromethane or CH 3 CN to produce compound 4

and
(4) contacting the compound 4 with propiolic acid with n-BuOH or t-Amyl-OH as solvent and heating to produce compound 5

and
(5) contacting the compound 5 with DBU or DBN in MeOH or EtOH for benzoate ester hydrolysis to yield the compound of Formula I.

2 . The compound of Formula I prepared according to the process of claim 1 .

Assignees

• Bristol Myers Squibb Co

Inventors

• Ortiz Adrian
• Benkovics Tamas
• Eastgate Martin D

Classifications

• C07D407/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07C315/04

  by reactions not involving the formation of sulfone or sulfoxide groups · CPC title

• C07C319/14

  of sulfides · CPC title

• C07C319/20

  by reactions not involving the formation of sulfide groups · CPC title