Ethanolamine → Tert-butyl 3-{[(benzyloxy)carbonyl](2-hydroxyethyl)amino}propanoate

6.11 g (100 mmol) of ethanolamine were cooled (0° C.), treated with 14.52 ml (100 mmol) of ter-butyl-acrylate and stirred 15 min at this temperature. During warming up to room temperature the reaction started and was kept with cooling at 25-30° C. and then stirred 18 h at room temperature. The oil was dissolved in 500 ml of tetrahydrofuran and 500 ml of water, 27.42 (110 mmol) of N-(benzyloxycarbonyloxy)succinimide were added at 0° C. followed by 27.88 ml (200 mmol) of triethlamine. The reaction was stirred at room temperature over 3 h, then partitioned between 10% aq. potassium hydrogensulfate solution and diethyl ether (3×). The organic phases were washed with 10% aq. potassium hydrogensulfate solution, sat. aq. sodium hydrogencarbonate solution, 10% aq. sodium chloride solution, dried over Na2SO4 evaporated and purified by flash silica gel column (n-heptane/ethyl acetate 4:1 to 1:1) to yield 27.53 g (85%) of the titled compound as light yellow oil. MS: 324.2 (MH+).

1. temperaturewith cooling at 25-30° C.
2. stirringstirred 18 h at room temperature
3. stirringThe reaction was stirred at room temperature over 3 h
4. custompartitioned between 10% aq. potassium hydrogensulfate solution and diethyl ether (3×)
5. washThe organic phases were washed with 10% aq. potassium hydrogensulfate solution, sat. aq. sodium hydrogencarbonate solution, 10% aq. sodium chloride solution
6. dry with materialdried over Na2SO4
7. customevaporated
8. custompurified by flash silica gel column (n-heptane/ethyl acetate 4:1 to 1:1)

ORD-Eintrag

ord-ae0c80902944447b91c314c3f75cebd1

Quelldatensatz

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08445674B2