Hydrochloric Acid → HCID 178484576, Verbindung

HRID 1441372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1441372
[CH3:1][N:2]([CH3:17])[C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)=[O:4].Cl.O1CCOCC1.[N:25]#[C:26][NH2:27]>CCO.C(#N)C>[CH3:1][N:2]([CH3:17])[C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:26]([NH2:27])=[NH:25])=[CH:14][CH:15]=1)=[O:4]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 9864CyanamideHCID 312751,4-DioxaneHCID 68686439(S)-1-(4-Amino-phenyl)-pyrrolidine-2-carboxylic acid dimethylamide

Produkt 1

HCID 178484576HCID 178484576, VerbindungAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To (S)-1-(4-Amino-phenyl)-pyrrolidine-2-carboxylic acid dimethylamide (Method 53; 0.67 g) was added acetonitrile (20 ml) and EtOH (2 ml). HCl in dioxane (0.86 ml, 3.48 mmol) was added and the reaction was stirred for 10 minutes, HCl salt precipitated. Cyanamide (0.2 g, 4.9 mmol) was added and the reaction was heated at reflux over the weekend. The black reaction was filtered and the black HCl salt was dissolved in water (5 ml) and basified with NaHCO3 (20 ml) solution. No solid was observed; the aqueous was further basified to pH 14 with KOH, extracted with DCM (2×100 ml), dried and solvent removed in vacuo to yield the title compound as a black gum (0.50 g, 63%). M/z 276.

Aufarbeitung

  1. customHCl salt precipitated
  2. temperaturethe reaction was heated
  3. temperatureat reflux over the weekend
  4. customThe black reaction
  5. filtrationwas filtered
  6. dissolutionthe black HCl salt was dissolved in water (5 ml)
  7. extractionextracted with DCM (2×100 ml)
  8. customdried
  9. customsolvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e616d8ed757440d0b10109c81c36ef9a
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07655652B2

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