Hydrochloric Acid → [Benzyl-(2-hydroxy-1-methylethyl)-amino]acetic acid tert-butyl ester

Temperature

0 °C

To a mixture of an optically-active compound of 2-benzylaminopropan-1-ol (111.2 g), potassium carbonate (111.6 g) and N,N-dimethylformamide (556 ml) cooled to 0° C. was added dropwise bromoacetic acid tert-butyl ester (109 ml) over 20 minutes, and the mixture was stirred at room temperature for 19.5 hours. The mixture was acidified by the addition of 2M aqueous hydrochloric acid solution and 6M aqueous hydrochloric acid solution to pH 2, and washed with toluene (1000 ml). The separated organic layer was extracted with 0.1M aqueous hydrochloric acid solution (300 ml). The combined aqueous layer was adjusted to pH 10 by 4M aqueous sodium hydroxide solution, and extracted with ethyl acetate (700 ml). The organic layer was sequentially washed with water (900 ml) and saturated aqueous sodium chloride solution (500 ml). The separated aqueous layer was extracted with ethyl acetate (400 ml) again. The combined organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the titled compound (160.0 g).

1. washwashed with toluene (1000 ml)
2. extractionThe separated organic layer was extracted with 0.1M aqueous hydrochloric acid solution (300 ml)
3. extractionextracted with ethyl acetate (700 ml)
4. washThe organic layer was sequentially washed with water (900 ml) and saturated aqueous sodium chloride solution (500 ml)
5. extractionThe separated aqueous layer was extracted with ethyl acetate (400 ml) again
6. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure

ORD record

ord-63dd33b81ced4696996c4fe58b16438a

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609647B2