Thionyl Chloride → [Benzyl-(2-chloro-1-methylethyl)-amino]acetic acid tert-butyl ester

To a solution of an optically-active compound of [benzyl-(2-hydroxy-1-methylethyl)-amino]acetic acid tert-butyl ester (160.0 g) in chloroform (640 ml) cooled to 0° C. was added dropwise thionyl chloride (50.0 ml), and the mixture was stirred at 60° C. for 2 hours. The reaction mixture was cooled to 0° C. Then, thereto were added saturated aqueous sodium bicarbonate solution (1000 ml) and chloroform (100 ml), and the mixture was stirred. The separated organic layer was washed with saturated aqueous sodium chloride solution (500 ml), and the aqueous layer was extracted with chloroform (450 ml) again. The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the titled compound (172.9 g).

1. temperatureThe reaction mixture was cooled to 0° C
2. stirringthe mixture was stirred
3. washThe separated organic layer was washed with saturated aqueous sodium chloride solution (500 ml)
4. extractionthe aqueous layer was extracted with chloroform (450 ml) again
5. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure

ORD record

ord-4197bcef3b754de489e2486bb8ec9e1a

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609647B2