Ethanolamine → [(R)-1-(2-hydroxy-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

Temperature

60 °C

In a round-bottomed flask, Boc-D-alanine (1.0 g, 5.29 mmol was dissolved in THF (40 ml) and 1,1′-carbonyldiimidazole (1.03 g, 6.34 mmol) was added. The reaction mixture was stirred at 60° C. for 45 min then cooled to room temperature and ethanolamine (3.2 ml, 52.9 mmol) was added. The reaction mixture was stirred at room temperature overnight then quenched with 1 M aqueous HCl (15 ml) and extracted with dichloromethane. The organic layer was washed with 1 M aqueous HCl, water and brine. The aqueous layers were back-extracted with dichloromethane (2×). The organic layers were combined, dried over sodium sulfate, filtered and concentrated to afford 1.11 g (90%) of [(R)-1-(2-hydroxy-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester as a colorless oil.

1. temperaturethen cooled to room temperature
2. stirringThe reaction mixture was stirred at room temperature overnight
3. customthen quenched with 1 M aqueous HCl (15 ml)
4. extractionextracted with dichloromethane
5. washThe organic layer was washed with 1 M aqueous HCl, water and brine
6. extractionThe aqueous layers were back-extracted with dichloromethane (2×)
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-2a362d54be0a4dc5b268f21e6e5c43fc

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658646B2