Benzaldehyde → HCID 86746675, compound

HRID 2226990Notes

Reaction equation

HRID 2226990 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:10][C@H:11]([C:15]([NH2:17])=[O:16])[CH2:12][CH2:13][CH3:14].CCN(CC)CC>>[CH:1](=[N:17][C:15](=[O:16])[C@H:11]([CH2:12][CH2:13][CH3:14])[NH2:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 56777018L-Norvalinamide--hydrogen chloride (1/1)

Product 1

HCID 86746675HCID 86746675, compoundYield 95.9%

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-bdb0c26448fb432ea61749b5e0ef5af5
Source dataset
uspto-grants-1994_09
Patent number
US05350851

Reaction notes

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