Benzaldehyde → HCID 86746675, compound

HRID 1614705Notes

Reaction equation

HRID 1614705 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

5

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 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.

Workup

  1. customwas then evaporated to 15 mL, and 175 mL Et2O
  2. additionadded
  3. filtrationAfter filtration
  4. washthe precipitated salts were washed with additional Et2O, solvent
  5. customevaporated from the combined filtrate, and residual benzaldehyde
  6. customremoved under high vacuum

Sources & evidence

ORD record
ord-0b0a889033a54637911190dd68aa4ffe
Source dataset
uspto-grants-1993_03
Patent number
US05198547

Reaction notes

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