Guanidine Hydrochloride → HCID 178508871, Verbindung

HRID 2059760

Reaktionsgleichung

Reaktionsgleichung von HRID 2059760
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].O=[C:7]1[CH:18]([C:19](OC)=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][C:8]21[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:4][C:3]1[N:5]=[C:19]([OH:20])[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:8]3([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)[C:7]=2[N:2]=1

Komponenten

5

Edukt 3

HCID 5742Guanidine HydrochlorideHCID 11430Potassium CarbonateHCID 57429461Methyl 7-oxospiro[5.6]dodecane-8-carboxylate

Produkt 1

HCID 178508871HCID 178508871, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of guanidine hydrochloride (430 mg, 4.5 mmol), the product from Example 16B (430 mg, 1.8 mmol), and potassium carbonate (623 mg, 4.5 mmol) in DMF (8 mL) was heated at 100° C. for 16 hours. Then, the temperature was raised to 120° C. for 2 hours. The mixture was cooled to ambient temperature and filtered through a layer of diatomaceous earth, then the filter pad was washed with a small amount of DMF. The filtrate was concentrated under reduced pressure, and the residue was chromatographed on silica gel (10:45:45 MeOH/CH2Cl2/EtOAc, eluant) to provide the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) ppm 10.62 (s, 1 H), 6.04 (s, 2 H), 2.57-2.64 (m, 2 H), 1.93-2.05 (m, 2 H), 1.60-1.71 (m, 4 H), 1.35-1.57 (m, 9 H), 1.15-1.28 (m, 1 H). MS (DCI+) m/z 248 (M+H).

Aufarbeitung

  1. temperatureThe mixture was cooled to ambient temperature
  2. filtrationfiltered through a layer of diatomaceous earth
  3. washthe filter pad was washed with a small amount of DMF
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was chromatographed on silica gel (10:45:45 MeOH/CH2Cl2/EtOAc, eluant)

Quellen und Nachweise

ORD-Eintrag
ord-20a112029c3144edba1b63335cd378cf
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278313B2

Verknüpfte Notizen

Wird geladen…