Hydrochloric Acid → N-[N-(3-hexadecanoyloxyoctadecanoyl)-beta-alanyl]-L-threonine

HRID 1903532Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1903532
[C:1]([O:18][CH:19]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:20][C:21]([OH:23])=O)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].ON1C(=O)CCC1=O.[NH2:47][CH2:48][CH2:49][C:50]([NH:52][C@H:53]([C:57]([OH:59])=[O:58])[C@@H:54]([CH3:56])[OH:55])=[O:51].Cl>O1CCOCC1.CN(C)C=O.O.C(N(CC)CC)C>[C:1]([O:18][CH:19]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:20][C:21]([NH:47][CH2:48][CH2:49][C:50]([NH:52][C@H:53]([C:57]([OH:59])=[O:58])[C@@H:54]([CH3:56])[OH:55])=[O:51])=[O:23])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 80170N-HydroxysuccinimideHCID 134890283-Hexadecanoyloxyoctadecanoic acidHCID 18649800beta-alanyl-L-threonine

Produkt 1

HCID 54384255N-[N-(3-hexadecanoyloxyoctadecanoyl)-beta-alanyl]-L-threonineAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

3-Hexadecanoyloxyoctadecanoic acid (150 mg) prepared by the method described in Preparation 2-(3) and N-hydroxysuccinimide (38 mg) were dissolved in dioxane (3 ml). N,N-Dicyclohexylcarbodiimide (68 mg) was added thereto under ice cooling. The mixture was reached to room temperature and stirred at ambient temperature overnight. The crystallized urea was filtered off and the filtrate was concentrated to give a residue which was dissolved in N,N-dimethylformamide (7 ml). To this solution was added a solution of N-β-alanyl-L-threonine (110 mg) and triethylamine (100 μl) in water (5 ml) at 0° C. The resulting mixture was reached to room temperature and stirred at ambient temperature overnight. The reaction mixture was acidified with 1 N hydrochloric acid, extracted with ethyl acetate, washed with water and dried over magnesium sulfate. Ethyl acetate was distilled off to give a residue which was subjected to preparative thin layer chromatography (Merck, 0.25 mm×5) and eluted with a mixture of benzene, dioxane and acetic acid (10:5:1). The band containing the object compound was extracted with a mixture of methanol and chloroform (3:7) and the solvent was evaporated off under reduced pressure to afford powder of N-[N-(3-hexadecanoyloxyoctadecanoyl)-β-alanyl]-L-threonine (95 mg).

Aufarbeitung

  1. customdescribed in Preparation 2-(3)
  2. customwas reached to room temperature
  3. filtrationThe crystallized urea was filtered off
  4. concentrationthe filtrate was concentrated
  5. customto give a residue which
  6. customwas reached to room temperature
  7. stirringstirred at ambient temperature overnight
  8. extractionextracted with ethyl acetate
  9. washwashed with water
  10. dry with materialdried over magnesium sulfate
  11. distillationEthyl acetate was distilled off
  12. customto give a residue which
  13. washeluted with a mixture of benzene, dioxane and acetic acid (10:5:1)
  14. additionThe band containing the object compound
  15. extractionwas extracted with a mixture of methanol and chloroform (3:7)
  16. customthe solvent was evaporated off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2ae09da88d194458a4a2db096250a931
Quelldatensatz
uspto-grants-1984_03
Patentnummer
US04436726

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