Benzaldehyde → HCID 67269069, compound

To (2R,3S)-2-amino-3-hydroxybutanoic acid (14.7 g, 123 mol) in NaOH (50%, 70 mL) was added benzaldehyde (14 mL, 123 mmol). The white slurry was stirred at room temperature for 18 h and then cooled to 0° C. NaBH4 (675 mg, 17.9 mmol) was added in two portions over 10 minutes Cooling bath was removed and the thick slurry was stirred at room temperature for 40 minutes and addition NaBH4 (659 mg, 17.4 mmol) was added and stirred at 0° C. for 40 minutes Benzaldehyde (10 mL, 99 mmol) was added, cooled to 0° C. and additional NaBH4 (700 mg, 18.5 mmol) was added. After 5 minutes warmed up to room temperature and stirred for 2 hour. The reaction mixture was acidified with HCl (conc.) to pH of (about 3) and then filtered precipitate, washed with cold water and dried to give (2R,3S)-2-(benzylamino)-3-hydroxybutanoic acid (3.4 g, 13.2%) of white solid. MS [M+H] found 210.

1. temperaturecooled to 0° C
2. temperatureCooling bath
3. customwas removed
4. stirringthe thick slurry was stirred at room temperature for 40 minutes
5. additionwas added
6. additionwas added
7. temperaturecooled to 0° C.
8. temperatureAfter 5 minutes warmed up to room temperature
9. stirringstirred for 2 hour
10. filtrationfiltered precipitate
11. washwashed with cold water
12. customdried

ORD record

ord-2d3afa1785be4806af88397d1a108bc3

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268819B2