(S)-2-Amino-3-(4-but-2-ynyloxy-phenyl)-N-methyl-propionamide hydrochloride → (S)-2-amino-3-(4-butoxy-phenyl)-N-methyl-propionamide

(S)-2-Amino-3-(4-but-2-ynyloxy-phenyl)-N-methyl-propionamide hydrochloride (2.00 g, 7.07 mmol) was dissolved in methanol (100 mL), and Pd/C (230 mg) was then added at room temperature. After stirring for 17 hours under a hydrogen atmosphere, insoluble material was filtered off, and washed with methanol (3.0 mL). The filtrate was concentrated under reduced pressure, and then dissolved in ethyl acetate (150 mL). The solution was washed with sodium bicarbonate (100 mL) and a saturated aqueous solution (50 mL) of sodium chloride in this order, then dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off under reduced pressure to obtain 1.77 g of the title compound (7.07 mmol, quant.).

1. filtrationinsoluble material was filtered off
2. washwashed with methanol (3.0 mL)
3. concentrationThe filtrate was concentrated under reduced pressure
4. dissolutiondissolved in ethyl acetate (150 mL)
5. washThe solution was washed with sodium bicarbonate (100 mL)
6. dry with materiala saturated aqueous solution (50 mL) of sodium chloride in this order, then dried over anhydrous sodium sulfate
7. filtrationfiltered
8. distillationThe solvent was distilled off under reduced pressure

ORD record

ord-7fc48c4de6ed4d549d02ce411639a48b

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266853B2