Ammonium Chloride → Ethyl 4-(1,1-dimethylethylsulfinamido)-4-(2-fluoro-6-methoxyphenyl)-2-methylbutanoate

Temperature

-78 °C

A cooled (−78° C.) solution of commercially available 2-bromo-1-fluoro-3-methoxybenzene (2.642 g; 12.90 mmol) in anh. THF (60 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (8.05 ml; 12.90 mmol). The resulting solution was further stirred at −78° C. for 5 min. A solution of ethyl 4-((tert-butylsulfinyl)imino)-2-methylbutanoate (2.550 g; 10.30 mmol) in anh. THF (20 ml) was then added dropwise to the cooled reaction mixture, and stirring at −78° C. was continued for 45 min. The resulting reaction mixture was treated successively with aq. sat. NH4Cl (75 ml), Et2O (250 ml) and water (75 ml). The separated organic layer was then washed with brine (75 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=30/1) afforded ethyl 4-(1,1-dimethylethylsulfinamido)-4-(2-fluoro-6-methoxyphenyl)-2-methylbutanoate as a yellow oil. LC-MS (conditions A): tR=0.81 min. and [M+H]+: 374.02 g/mol; tR=0.83 min. and [M+H]+: 374.34 g/mol (mixture of diastereoisomers).

1. stirringstirring at −78° C.
2. waitwas continued for 45 min
3. customThe resulting reaction mixture
4. washThe separated organic layer was then washed with brine (75 ml)
5. dry with materialdried over anh. MgSO4
6. filtrationfiltered
7. concentrationconcentrated to dryness under reduced pressure
8. customPurification by FC (DCM/MeOH=30/1)

ORD record

ord-2ffc6aca81ad43f49d783b71c6c28723

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242970B2