Benzaldehyde → N-benzyl-L-alanine

L-Alanine (44.6 g, 0.5 mole)) was taken up in 250 mL 2N-NaOH to which was added benzaldehyde (50 mL, 0.5 mole). The resulting suspension was stirred at room temperature for approximately 20 minutes. After this period a pale yellow solution resulted. This solution was cooled in an ice/acetone bath and sodium borohydride (5.7 g, 0.15 mole) added in 1.0 g portions while keeping the temperature below 15° C. A large flask is necessary as a good deal of foaming takes place during the course of the reaction. The above process was repeated with the same quantities of benzaldehyde and sodium borohydride. However, this time after the addition of the sodium borohydride, the resulting solution was stirred for about 11/2 hours at room temperature and then washed with either (100 mL, ×2). The ether extracts were discarded and the aqueous phase acidified with 6N-HCl to pH 6-7. The product precipitated out of the solution. The resulting mixture was left overnight in the refrigerator and filtered the following morning. The product was washed with a little cold water and air dried. Yield 67 g (75%).

1. customAfter this period a pale yellow solution resulted
2. temperatureThis solution was cooled in an ice/acetone bath
3. customthe temperature below 15° C
4. customA large flask is necessary as a good deal of foaming
5. customduring the course of the reaction
6. stirringthe resulting solution was stirred for about 11/2 hours at room temperature
7. washwashed with either (100 mL, ×2)
8. customThe product precipitated out of the solution
9. waitThe resulting mixture was left overnight in the refrigerator
10. filtrationfiltered the following morning
11. washThe product was washed with a little cold water and air
12. customdried

ORD record

ord-df66fa789b2243158aa0d5dfaad23753

Source dataset

uspto-grants-1989_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04857440