StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Hydrochloric Acid → Treprostinil

HRID 245602
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 245602
[OH:1][C@H:2]1[C@H:18]([CH2:19][CH2:20][C@@H:21]([OH:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C@H:5]2[CH2:6][C:7]3[C:12]([CH2:13][C@H:4]2[CH2:3]1)=[C:11]([O:14][CH2:15][C:16]#N)[CH:10]=[CH:9][CH:8]=3.[OH-:28].[K+].Cl.C[OH:32]>>[CH3:26][CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]([OH:27])[CH2:20][CH2:19][C@H:18]1[C@H:2]([OH:1])[CH2:3][C@H:4]2[C@@H:5]1[CH2:6][C:7]1[C:12]([CH2:13]2)=[C:11]([O:14][CH2:15][C:16]([OH:32])=[O:28])[CH:10]=[CH:9][CH:8]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 11314741Descarboxymethyl Cyanomethyl Treprostinil

Produkt 1

HCID 6918140TreprostinilAusbeute 81 %

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

2-((1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalen-5-yloxy)acetonitrile (2 g, 0.05 mol) in methanol (18 ml) was treated with 20% KOH (6 ml) and refluxed for 3 hr. The reaction was then cooled to 10° C. and 3N HCl was added slowly until pH=˜8. The solvent was removed in vacuo. Ethyl acetate and brine were added and then 3N HCl was added slowly until pH=2. The reaction mixture was extracted with ethyl acetate. The combined ethyl acetate extracts were dried over anhydrous magnesium sulfate. The solid was filtered off. The solvent was evaporated off under vacuum. The crude product was purified by crystallization from ethanol/H2O. The titled compound was obtained in a crystalline form. Yield: 81%.

Aufarbeitung

  1. temperaturerefluxed for 3 hr
  2. customThe solvent was removed in vacuo
  3. additionEthyl acetate and brine were added
  4. addition3N HCl was added slowly until pH=2
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. dry with materialThe combined ethyl acetate extracts were dried over anhydrous magnesium sulfate
  7. filtrationThe solid was filtered off
  8. customThe solvent was evaporated off under vacuum
  9. customThe crude product was purified by crystallization from ethanol/H2O

Quellen und Nachweise

ORD-Eintrag
ord-56ec96b01565429a87d2fb3bc9825319
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08658837B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion