Benzyl bromoacetate → N-allylglycine benzyl ester hydrochloride

To a solution of allylamine hydrochloride (5.0 g, 53.4 mmol) in tetrahydrofuran (100 mL) was added diisopropylethylamine (10 mL) and bromoacetic acid benzyl ester (3.06 g, 13.3 mmol) at 0° C. and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure. The residue was added ethyl acetate and 1 N-hydrochloric acid solution, the organic layer was separated, and the aqueous layer was extracted two times with ethyl acetate. The organic layers were combined, washed with sodium thiosulfate solution and brine, and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography, and to the obtained oil was added 4N-Hydrogen chloride in 1,4-Dioxane (3.5 mL). The mixture was concentrated under reduced pressure and lyophilized to give the title compound (2.12 g, 8.79 mmol, 66%).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionThe residue was added ethyl acetate and 1 N-hydrochloric acid solution
3. customthe organic layer was separated
4. extractionthe aqueous layer was extracted two times with ethyl acetate
5. washwashed with sodium thiosulfate solution and brine
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe obtained residue was purified by silica gel column chromatography
9. additionto the obtained oil was added 4N-Hydrogen chloride in 1,4-Dioxane (3.5 mL)
10. concentrationThe mixture was concentrated under reduced pressure

ORD record

ord-0ca97787a55046c094ddda6e81b97fa5

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09227949B2