Triethylamine → HCID 87076249, compound

Temperature

-78 °C

To a stirred solution of DCM, (R)-methyl mandelate (1.48 g, 8.92 mmol), and triethylamine (2.02 g, 20.0 mmol), in DCM (30 ml) under a nitrogen atmosphere at −78° C. was added dropwise bromoacetyl bromide (3.03 g, 15.0 mmol). After stirring at −78° C. for 5 h, the reaction mixture was allowed warm up to −20° C. and quenched by addition of water (20 mL). The organic phase was washed with distilled water (3×20 mL), saturated ammonium chloride (3×20 mL), saturated sodium bicarbonate (3×20 mL) and brine (2×20 mL). The organic phase was then dried over magnesium sulfate, filtered and solvents removed via rotary evaporation to yield a crude product in 84% yield (2.13 g, 7.42 mmol). Column chromatography was performed on the crude product (mobile phase: DCM:Hexane, 50:50) to give a pale yellow liquid at RT in 73% yield (1.85 g, 6.45 mmol).

1. temperaturethe reaction mixture was allowed warm up to −20° C.
2. customquenched by addition of water (20 mL)
3. washThe organic phase was washed with distilled water (3×20 mL), saturated ammonium chloride (3×20 mL), saturated sodium bicarbonate (3×20 mL) and brine (2×20 mL)
4. dry with materialThe organic phase was then dried over magnesium sulfate
5. filtrationfiltered
6. customsolvents removed via rotary evaporation

ORD record

ord-24e03b5936914e8e9eae14cb1d51dd59

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785655B2