Thionyl Chloride → Lysine dihydrochloride

HRID 2244510

Reaktionsgleichung

Reaktionsgleichung von HRID 2244510
S(Cl)([Cl:3])=O.[ClH:5].[NH2:6][C@H:7]([C:13]([OH:15])=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][NH2:12]>C(O)C>[ClH:3].[ClH:5].[NH2:6][C@H:7]([C:13]([OH:15])=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][NH2:12]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 69568L-Lysine monohydrochloride

Produkt 1

HCID 69567Lysine dihydrochlorideAusbeute 112,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

11.9 g of thionyl chloride are added in the cold to L-lysine hydrochloride (11 g) in 100 ml of ethanol and the mixture is refluxed for 3 h. After evaporation of the excess thionyl chloride and ethanol, the product is washed with heptane and then dried under vacuum to give 14.8 g of lysine bishydrochloride in which the acid group is esterified with ethanol. This product (4.9 g) is reacted with 7 g of the N-hydroxysuccinimide derivative of palmitic acid (Rn Cas 14464-31-4, available from Sigma) in an acetone/water mixture (80+40 ml respectively), in the presence of 7 g of triethylamine. After one night at room temperature, the product is precipitated by adding 1 N hydrochloric acid. After purification by passage over a silica column, 3.3 g of the desired product are recovered. Its structure is confirmed by NMR spectroscopy.

Aufarbeitung

  1. temperaturethe mixture is refluxed for 3 h
  2. customAfter evaporation of the excess thionyl chloride and ethanol
  3. washthe product is washed with heptane
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-06aee5e884ed40eca0c8bd7afdfacb62
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678882B2

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