Bromoacetonitrile → 6-Chloro-N-(cyanomethyl)-N-{(3S)-1-[(1S)-1-methyl-2-oxo-2-piperidin-1-ylethyl]-2-oxopyrrolidin-3-yl}naphthalene-2-sulfonamide

Temperature

-78 °C

A solution of 6-chloro-N-{(3S)-1-[(1S)-1-methyl-2-oxo-2-piperidin-1-ylethyl]-2-oxopyrrolidin-3-yl}naphthalene-2-sulfonamide (0.015 g) in THF (2 ml) was cooled to −78° C. under nitrogen, and treated with lithium bis(trimethylsilyl) amide (1.0M solution in THF; 0.042 ml), followed by bromoacetonitrile (0.019 g). The resultant solution was allowed to reach room temperature and stirred for a further 16 h. The mixture was then cooled to −78° C. and further lithium bis(trimethylsilyl) amide (0.042 ml) added. After reaching room temperature, the reaction mixture was stirred for a further 18 h and then quenched by the addition of methanol (1 ml). The resultant solution was concentrated under reduced pressure and the residue partitioned between water and DCM. The organic layer was separated, dried (over magnesium sulphate) and concentrated under reduced pressure. The residue was purified by mass directed preparative h.p.l.c to give the title compound (0.007 g) as a colourless gum.

1. customto reach room temperature
2. customAfter reaching room temperature
3. stirringthe reaction mixture was stirred for a further 18 h
4. customquenched by the addition of methanol (1 ml)
5. concentrationThe resultant solution was concentrated under reduced pressure
6. customthe residue partitioned between water and DCM
7. customThe organic layer was separated
8. dry with materialdried (over magnesium sulphate)
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by mass

ORD record

ord-df5abb0d36a745ff964e2f8fa27724ba

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07084139B2