tert-Butyl bromoacetate → HCID 53800105, compound

To a −78° C. solution of methyl 4-methylthiobutyrate (1.48 g, 10.0 mmol) in THF (20 mL) was added sodium bis(trimethylsilyl)amide (1.0 M in THF, 11 mL). After 30 min, tert-butyl bromoacetate (2.34 g, 12.0 mmol) was added to the reaction, and the reaction mixture was gradually warmed to the room temperature over 6 hours. The reaction mixture was then partitioned between ethyl acetate (80 mL) and water (20 mL). The organic layer was washed with water (2×20 mL), brine (20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by column chromatography with 5% ethyl acetate in hexane to give the title compound (1.21 g, 46%).

1. customThe reaction mixture was then partitioned between ethyl acetate (80 mL) and water (20 mL)
2. washThe organic layer was washed with water (2×20 mL), brine (20 mL)
3. dry with materialdried over anhydrous magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customThe residue was purified by column chromatography with 5% ethyl acetate in hexane

ORD record

ord-eb4138a132ed4de1936a9b22ebe3d2d5

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06310095B1