Potassium bis(trimethylsilyl)amide → HCID 118005583, compound

To a solution of methyl 2-(2-(benzyloxy)acetamido)-5-bromobenzoate (15 g, 39.7 mmol, Intermediate 11: step a) in THF (198 mL) was added KHMDS (1 M in THF, 119 mL, 119 mmol). The resulting solution was stirred at room temperature for 40 minutes and then additional KHMDS (19.8 mL, 19.8 mmol) was added and stirring continued at room temperature for 2 hours. The mixture was quenched with water (225 mL) and the layers were separated. The aqueous layer was acidified with 1 N aqueous HCl to pH 2-3. Some of the title compound precipitated out of solution and was collected by filtration. The aqueous was then extracted with EtOAc (3×200 mL). The organics were combined with the solid collected previously and sonicated. The solution was dried (Na2SO4), filtered and concentrated to dryness to provide the title compound as a yellow solid.

1. stirringstirring
2. waitcontinued at room temperature for 2 hours
3. customThe mixture was quenched with water (225 mL)
4. customthe layers were separated
5. customSome of the title compound precipitated out of solution
6. filtrationwas collected by filtration
7. extractionThe aqueous was then extracted with EtOAc (3×200 mL)
8. customcollected previously
9. customsonicated
10. dry with materialThe solution was dried (Na2SO4)
11. filtrationfiltered
12. concentrationconcentrated to dryness

ORD record

ord-4bec8e3e1ef14423a30d14034a9a8abd

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403816B2