Decanoic Acid → Sumatriptan caprate

HRID 1383789

Reaktionsgleichung

Reaktionsgleichung von HRID 1383789
[CH3:1][NH:2][S:3]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:15][CH:14]=[C:13]([CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[C:11]=2[CH:12]=1)(=[O:5])=[O:4].[OH:21][C:22]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:23]>C(OCC)(=O)C>[CH3:1][NH:2][S:3]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:15][CH:14]=[C:13]([CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[C:11]=2[CH:12]=1)(=[O:5])=[O:4].[O-:23][C:22]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:21]

Komponenten

4

Edukt 2

HCID 2969Decanoic AcidHCID 5358Sumatriptan2×

Produkt 1

HCID 21188875Sumatriptan caprate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

Sumatriptan base ((2.29g; 7.75 mmol) was dissolved in boiling ethyl acetate (300 mL) with stirring. Capric acid (1.33 g; 7.75 mmol) was dissolved in ethyl acetate (10 mL) and added to the sumatriptan base solution in one portion. The hot solution was stirred for a further 10 minutes and allowed to cool to room temperature. Evaporation of the solvent by rotary evaporation rave a pale yellow oil. Hexane (50 mL) was added and a white precipitate formed that was filtered off under vacuum. The precipitate was washed with hexane and allowed to dry at room temperature to give sumatriptan caprate as a pale yellow solid (2.79 g; 77.4%). The sumatriptan caprate was characterised by DSC and FT-IR. DSC gave a single, sharp endotherm with the onset at 94.6° C. The FT-IR differed significantly from that of the sumatriptan base.

Aufarbeitung

  1. stirringThe hot solution was stirred for a further 10 minutes
  2. customEvaporation of the solvent
  3. customby rotary evaporation
  4. additionHexane (50 mL) was added
  5. customa white precipitate formed
  6. filtrationthat was filtered off under vacuum
  7. washThe precipitate was washed with hexane
  8. customto dry at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-14b31f00405b435191834643f37b7289
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255502B1

Verknüpfte Notizen

Wird geladen…