Phosphate → HCID 86746434, compound

A solution of meso 2,3-dimercaptosuccinic acid (4.55 g, 25 mmol) in 50 mL dichloromethane or tetrahydrofuran or other similar aprotic solvents containing p-toluenesulfonic acid monohydrate (0.048 g, 0.252 mmol) is cooled to -18° to -25° C. with constant stirring. Ethyl vinyl ether (4.8 mL, 50 mmol) in 50 mL dichloromethane or other aprotic solvents is added dropwise to the cold solution over a period of 1.5 to 2 hours. The stirring is continued for an additional 30 minutes with the temperature maintained in the -18° to -25° C. range. Then 20 mL of pH 7 phosphate buffer is added, and the reaction mixture is allowed to warm with stirring for 10 to 15 minutes. The reaction mixture is then poured into a flask containing 100 mL of ethyl acetate and 25 mL of deionized water. The layers are separated and the aqueous portion is extracted three times, each time with 50 mL ethyl acetate. The organic layers are combined, washed with water and then brine. The washed ethyl acetate extract is then dried over anhydrous sodium sulfate. Removal of the solvent gives 2 to 3 g of bis S-(1-ethoxyethyl) 2,3-dimercaptosuccinic acid. The material is used without further purification.

1. temperatureis cooled to -18° to -25° C. with constant stirring
2. temperaturemaintained in the -18° to -25° C. range
3. temperatureto warm
4. additionThe reaction mixture is then poured into a flask
5. customThe layers are separated
6. extractionthe aqueous portion is extracted three times
7. washwashed with water
8. extractionThe washed ethyl acetate extract
9. dry with materialis then dried over anhydrous sodium sulfate
10. customRemoval of the solvent

ORD record

ord-4c41e790cd1842ffb9da058e485f1a3b

Source dataset

uspto-grants-1992_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05175256