Acetic Acid → Bazedoxifene Acetate

HRID 339140

Reaktionsgleichung

Reaktionsgleichung von HRID 339140
[CH3:1][C:2]1[C:3]2[CH:4]=[C:5]([OH:35])[CH:6]=[CH:7][C:8]=2[N:9]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:23][CH:24]=2)[C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1.[C:36]([OH:39])(=[O:38])[CH3:37]>CC(C)=O>[CH3:1][C:2]1[C:3]2[CH:4]=[C:5]([OH:35])[CH:6]=[CH:7][C:8]=2[N:9]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)=[CH:21][CH:20]=2)[C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1.[CH3:37][C:36]([OH:39])=[O:38]

Komponenten

4

Edukt 2

HCID 176Acetic AcidHCID 154257Bazedoxifene2×

Produkt 1

HCID 154256Bazedoxifene Acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Reaktionsbedingungen

Temperatur
52.5 °C

Versuchsvorschrift

Bazedoxifene free base from example 17 or from example 19 (10 g, 21.2 mmol) was suspended in acetone (80 ml) and heated to 50-55° C. After getting a clear solution, a mixture of acetic acid (1.4 g, 23.3 mmol) and acetone (10 ml) was added slowly. Then the reaction mixture was allowed to cool at 20-25° C., stirred for 2 hrs, filtered the product formed, washed with acetone (20 ml) and dried under vacuum to afford the title compound in high yield and high purity (12.7 g, 95%) M.R: 176-181° C. HPLC: 99.9%.

Aufarbeitung

  1. additionwas added slowly
  2. temperatureto cool at 20-25° C.
  3. filtrationfiltered the product
  4. customformed
  5. washwashed with acetone (20 ml)
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-caeb91aa393c43648984eab217e048c1
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889896B2

Verknüpfte Notizen

Wird geladen…