Sulfuric Acid → N-(1-Oxododecyl)-L-valine

HRID 15616

Reaktionsgleichung

Reaktionsgleichung von HRID 15616
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].[OH-].[Na+].[C:11](Cl)(=[O:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].S(=O)(=O)(O)O>CC(C)=O.O>[C:11]([NH:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4])(=[O:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Komponenten

7

Edukt 4

HCID 1118Sulfuric AcidHCID 6287L-ValineHCID 8166Dodecanoyl chlorideHCID 14798Sodium Hydroxide2×

Produkt 1

HCID 26658N-(1-Oxododecyl)-L-valineAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

294 g (2.51 mol) of L-valine was dissolved into 786 g of ion-exchange water, 358 g (2.42 mol) of an aqueous solution of 27% sodium hydroxide and 363 g of acetone. With stirring the solution, 533 g (2.43 mol) of lauroyl chloride and 358 g (2.47 mol) of an aqueous solution of 27% sodium hydroxide were simultaneously added dropwise thereto so that pH=12±0.2 and the temperature is kept at 19 to 20° C. After completion of the addition, the solution was stirred at 20° C. for 60 minutes. Then, it was heated up to 40° C., and 171 g of 75% sulfuric acid was added thereto in order to adjust pH=1.5. The layers of the oily substance and water phase that separated at 60° C. were split, and 1950 g of warm water of 60° C. was added to the oily substance. After the mixture was cooled down to 20° C., the precipitated solid substance was filtered out and washed with water. Then, the substance was vacuum-dried at 50° C. to obtain 710 g of N-lauroyl-L-valine (2.37 mol, yield 98%).

Aufarbeitung

  1. additionwere simultaneously added dropwise
  2. customis kept at 19 to 20° C
  3. additionAfter completion of the addition
  4. temperatureThen, it was heated up to 40° C.
  5. customThe layers of the oily substance and water phase that separated at 60° C.
  6. customwere split
  7. addition1950 g of warm water of 60° C. was added to the oily substance
  8. temperatureAfter the mixture was cooled down to 20° C.
  9. filtrationthe precipitated solid substance was filtered out
  10. washwashed with water
  11. customThen, the substance was vacuum-dried at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-c7aadb181c1c4d9682aa593e3b8dea41
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732637B2

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