Diethyl Ether → S-(2-(2-methoxyethoxy)ethyl)carbonyl-L-cysteine
Reaction equation
Cl.[NH2:2][C@H:3]([C:6]([OH:8])=[O:7])[CH2:4][SH:5].C[CH2:10][O:11]CC.CO[CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][C:22](Cl)=O>C(=O)(O)[O-].[Na+].O>[CH3:22][O:21][CH2:20][CH2:19][O:18][CH2:17][CH2:16][C:10]([S:5][CH2:4][C@@H:3]([C:6]([OH:8])=[O:7])[NH2:2])=[O:11]Participants
Conditions
- Temperature
- 0 °C
Procedure
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): 64.43 (m,11H), 4.24 (m, 2H), 3.83-3.47 (m, 8H), 3.41 (s, 3H).
Workup
- temperatureThe solution was cooled in an ice bath
- customto rise to 10° C.
- stirringstirred for an additionional two hours
- customThe solvents were then removed under reduced pressure
- washThe resulting solid was washed with methanol
- customthe methanol layer was evaporated
Sources & evidence
- ORD record
- ord-35fa26a58be343789152c324d21c3def
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07329727B2
Reaction notes
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