Ammonia → (S)-Benzyl-3-hydroxyglutaramate

Temperature

55 °C

Mixture of Benzyl alcohol (131.0 g), (S)-methyl-3-hydroxyglutaramate (100 g) and Tetraisopropyl orthotitanate (17.5 g) are mixed in a flask. The mixture was stirred under vacuum at 50-60° C. for about 5 hrs. The reaction mixture was cooled and diluted with dichloromethane (500 ml). The reaction mixture was added to a stirred solution of Tartaric acid (37 g in 370 ml DM water) and 500 ml dichloromethane mixture. The reaction mixture was stirred and pH was adjusted to 7.0-8.0 by Aq ammonia solution. Layers were separated. The organic phase was removed and the aqueous phase was extracted with dichloromethane. Combined organic layer was washed with Aq ammonia and tartaric acid solution followed by brine wash. The organic phase was dried over anhydrous sodium sulphate and evaporated under reduced pressure to yield oil. To this oil tert-butyl methyl ether (800 ml) was added, stirred, cooled, filtered and dried to give (S)-Benzyl-3-hydroxyglutaramate.

1. additionare mixed in a flask
2. temperatureThe reaction mixture was cooled
3. stirringThe reaction mixture was stirred
4. customLayers were separated
5. customThe organic phase was removed
6. extractionthe aqueous phase was extracted with dichloromethane
7. washCombined organic layer was washed with Aq ammonia and tartaric acid solution
8. washwash
9. dry with materialThe organic phase was dried over anhydrous sodium sulphate
10. customevaporated under reduced pressure
11. customto yield oil
12. stirringstirred
13. temperaturecooled
14. filtrationfiltered
15. customdried

ORD record

ord-5f7f646032a748e7953133e99985c07e

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273333B2