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

ORD record

ord-606a5dc91e0c43abad0d643f89d6bb89

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09024044B2