Diethyl Ether → S-(2-(2-methoxyethoxy)ethyl)carbonyl-L-cysteine

Temperature

0 °C

L-cysteine hydrochloride (2.00 g, 12.7 mmol) was dissolved in 1M aqueous sodium bicarbonate (25.4 ml) and the solution was diluted with water (75 mL). The solution was cooled in an ice bath and then covered with ether (50 ml). (2-(2-methoxyethoxy)ethyl) chloroformate (2.31 g, 12.7 mmol) was added to the solution in one portion with vigorous stirring for one hour at 0° C. The temperature was allowed to rise to 10° C. and stirred for an additionional two hours. The solvents were then removed under reduced pressure. The resulting solid was washed with methanol and the methanol layer was evaporated to yield the product as a white oil (2.21 g, 65%). FTIR: 1709 cm−1. 1H NMR (D2O): δ4.43 (m, 1IH), 4.24 (m, 2H), 3.833.47 (m, 8H), 3.41 (s, 3H).

1. temperatureThe solution was cooled in an ice bath
2. customto rise to 10° C.
3. stirringstirred for an additionional two hours
4. customThe solvents were then removed under reduced pressure
5. washThe resulting solid was washed with methanol
6. customthe methanol layer was evaporated

ORD record

ord-64e42c1c1d0f44b5ad8aa8938f01fb0c

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06686446B2