L-Aspartic Acid → N-(3,3-Dimethylbutyl)-L-aspartic acid

HRID 1421633Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1421633
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5].C(=O)(O)[O-].[Na+].[CH3:15][C:16]([CH3:21])([CH3:20])[CH2:17][CH:18]=O>O.CO.[Pd]>[CH2:18]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5])[CH2:17][C:16]([CH3:21])([CH3:20])[CH3:15]

Komponenten

7

Edukt 3

HCID 5960L-Aspartic AcidHCID 763353,3-DimethylbutanalHCID 516892Sodium Bicarbonate

Produkt 1

HCID 9815811N-(3,3-Dimethylbutyl)-L-aspartic acidAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysator2×HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

L-aspartic acid (4 g, 0.03 mol) was added to a Parr bottle containing a solution of sodium bicarbonate (5.04 g, 0.06 mol) in water (50 mL) to form a clear solution, with effervescence. A solution of 3,3-dimethylbutyraldehyde (3 g, 0.03 mol) in methanol (50 mL) was then added to the Parr bottle, followed by Pd/C (4% palladium on carbon, 50% wet, 0.4 g). The mixture was hydrogenated at 50 psi/room temperature for 2 days. If the reaction was not complete, fresh Pd/C (0.2 g) would be added and hydrogenation continued for an additional 8 hrs. The mixture was filtered through a Celite® bed, and the bed was washed with methanol (20 mL). The filtrate and washings were combined and concentrated under reduced pressure at 40-50° C. The pH of the remaining aqueous solution was adjusted to 3 with concentrated hydrochloric acid. The precipitated solid was filtered and dried in a vacuum oven at 50° C. for 4 hrs to give 4.75 g (73%) of crude N-neohexyl-L-aspartic acid. The crude product was slurried with aqueous ethanol (47.5, 80% ethanol, 20% water) for 15 minutes and filtered to give 3.3 g (51%) of >98% pure N-neohexyl-L-aspartic acid. M.P. 184-186° C.; [α]D +12.35 (c=1, water); NMR (D2O) δ3.37(t, 3H); 2.25-2.65 (m, 4H); 1.27-1.47 (m, 2H); 0.89(s, 9H); Anal. Calc'd. for C10H19NO4 ; C, 55.28; H, 8.81; N, 6.45; Found: C, 55.35; H, 8.86; N, 6.50.

Aufarbeitung

  1. customto form a clear solution
  2. waithydrogenation continued for an additional 8 hrs
  3. filtrationThe mixture was filtered through a Celite® bed
  4. washthe bed was washed with methanol (20 mL)
  5. concentrationconcentrated under reduced pressure at 40-50° C
  6. filtrationThe precipitated solid was filtered
  7. customdried in a vacuum oven at 50° C. for 4 hrs

Quellen und Nachweise

ORD-Eintrag
ord-fdbf3e49219f4a5a91ac944bc1af6191
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06077962

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