Ammonium Chloride → Methyl 5-([1,1'-biphenyl]-2-yl)-5-(1,1-dimethylethylsulfinamido)pentanoate

Temperatur

-78 °C

A cooled (−78° C.) solution of commercially available 2-iodo-1,1′-biphenyl (617 mg; 2.20 mmol) in anh. THF (5 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (1.50 ml; 2.40 mmol). The resulting solution was further stirred at −78° C. for 10 min. A solution of methyl 5-((tert-butylsulfinyl)imino)pentanoate (514 mg; 2.20 mmol) in anh. THF (2 ml) was added to the cooled reaction mixture, and stirring at −78° C. was continued for 10 min., and then at −20° C. for 2 h. The resulting reaction mixture was treated successively with aq. sat. NH4Cl (15 ml), Et2O (30 ml) and water (15 ml). The separated organic layer was then washed with brine (15 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=7/3) afforded methyl 5-([1,1′-biphenyl]-2-yl)-5-(1,1-dimethylethylsulfinamido)pentanoate as a yellow oil. LC-MS (conditions A): tR=0.85 min.; [M+H]+: 387.83 g/mol.

1. stirringstirring at −78° C.
2. waitwas continued for 10 min.
3. waitat −20° C. for 2 h
4. customThe resulting reaction mixture
5. washThe separated organic layer was then washed with brine (15 ml)
6. dry with materialdried over anh. MgSO4
7. filtrationfiltered
8. concentrationconcentrated to dryness under reduced pressure
9. customPurification by FC (heptane/AcOEt=7/3)

ORD-Eintrag

ord-cee37a7fb1ac483c9bb64648e3d802e4

Quelldatensatz

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09242970B2