Acetic Acid → HCID 105544108, compound

Temperature

60 °C

To a solution of β-alanine ethyl ester hydrochloride (1.00 g) in ethanol (13.5 mL), triethylamine (907 μL), 4-chlorophenylacetone (1.32 g), acetic acid (1.5 mL) and borane-2-picoline complex (1.39 g) were added successively and the mixture was stirred at 60° C. for 30 minutes. After being cooled to room temperature, the mixture was concentrated under reduced pressure. To the resulting residue, a saturated aqueous solution of sodium hydrogencarbonate was added and the mixture was extracted with chloroform twice. The combined organic layers were washed with saturated brine and dried over anhydrous sodium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0-95:5) to give the titled compound as a yellow oil (1.70 g).

1. temperatureAfter being cooled to room temperature
2. concentrationthe mixture was concentrated under reduced pressure
3. additionTo the resulting residue, a saturated aqueous solution of sodium hydrogencarbonate was added
4. extractionthe mixture was extracted with chloroform twice
5. washThe combined organic layers were washed with saturated brine
6. dry with materialdried over anhydrous sodium sulfate
7. customThe desiccant was removed by filtration
8. concentrationthe filtrate was concentrated under reduced pressure
9. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0-95:5)

ORD record

ord-00637ca1730f46e9987dd362844092a3

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422240B2