Benzaldehyde → HCID 86746675, compound

Reaction equation

[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C@H:10]([C:14]([NH2:16])=[O:15])[CH2:11][CH2:12][CH3:13].Cl.CCN(CC)CC>>[CH:1](=[N:16][C:14](=[O:15])[C@H:10]([CH2:11][CH2:12][CH3:13])[NH2:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 240Benzaldehyde

HCID 313Hydrochloric Acid

HCID 8471Triethylamine

HCID 447593HCID 447593, compound

Product 1

HCID 86746675HCID 86746675, compoundYield 72.9%

Conditions

Temperature: 23 °C

Procedure

Fresh benzaldehyde (4.02 g, 37.9 mmol) was added to a slurry of 4.0 g L-norvalinamide.HCl (XII) (26.2 mmol) in 70 mL 1-PrOH, followed by 4.08 mL Et3N (29.3 mmol). The mixture, which became clear after stirring at 23° C. for 70 minutes, was then evaporated to 15 mL, and 175 mL Et2O added. After filtration, the precipitated salts were washed with additional Et2O, solvent evaporated from the combined filtrate, and residual benzaldehyde removed under high vacuum to give 5.13 g N-benzylidene-L-norvalinamide (XIII) as a light yellow solid (UV λmax =249 nm in MeOH). The purity of this material was determined by normal phase HPLC.