L-Aspartic Acid → HCID 15454839, compound

HRID 1421636Notes

Reaction equation

HRID 1421636 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5].[CH3:10][C:11]([CH3:16])([CH3:15])[CH2:12][CH:13]=O>[Pd].CO.O>[CH2:13]([N:1]([CH2:13][CH2:12][C:11]([CH3:16])([CH3:15])[CH3:10])[C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5])[CH2:12][C:11]([CH3:16])([CH3:15])[CH3:10]

Participants

5

Reactant 2

HCID 5960L-Aspartic AcidHCID 763353,3-Dimethylbutanal

Product 1

HCID 15454839HCID 15454839, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a slurry of L-aspartic acid (4 g, 0.03 mol) in 1:1 methanol/water (80 mL) was added neat 3,3-dimethylbutyraldehyde (3 g, 0.03 mol), followed by Pd/C (4%, 50% wet, 0.5 g). The mixture was hydrogenated using H2 (50 psi) at room temperature for 2 days. The resulting reaction mixture was filtered through a Celite® bed, and the bed washed with methanol (50 mL) The filtrate and washings were combined and the methanol removed using a rotary evaporator under reduced pressure at 40-50° C. to provide the N,N-di-neohexyl L-aspartic acid as a solid precipitate in water. The solid was filtered, washed with water (2 mL) and dried in a vacuum oven at 50° C. for 4 hrs to provide 3.2 g of N,N-di-neohexyl L-aspartic acid (36%), M.P. 197-198° C., [α]D -3 (c=1, methanol). Anal. Calc'd. for C16H31NO4 ; C, 63.78; H, 10.29; N, 4.65. Found: C, 63.43; H, 10.29; N, 4.70

Workup

  1. customat room temperature
  2. customfor 2 days
  3. customThe resulting reaction mixture
  4. filtrationwas filtered through a Celite® bed
  5. washthe bed washed with methanol (50 mL) The filtrate and washings
  6. customthe methanol removed
  7. customa rotary evaporator under reduced pressure at 40-50° C.

Sources & evidence

ORD record
ord-aa4be11165a8499eb803ba5a953a2e3d
Source dataset
uspto-grants-2000_06
Patent number
US06077962

Reaction notes

Loading…