Ampicillin → Bacampicillin

HRID 478050

Reaktionsgleichung

Reaktionsgleichung von HRID 478050
[CH3:1][C:2]1([CH3:24])[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([C@H:13]([NH2:20])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:12])[C:8](=[O:9])[N:4]2[C@H:3]1[C:21]([OH:23])=[O:22].[K].[C:26](=[O:34])([O:31][CH2:32][CH3:33])[O:27][CH:28](Br)[CH3:29].C(=O)(O)[O-].[Na+]>C(#N)C>[CH3:29][CH2:28][O:27][C:26]([O:31][CH:32]([O:22][C:21]([C@@H:3]1[N:4]2[C:8]([C@@H:7]([NH:10][C:11]([C@H:13]([NH2:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:12])[C@H:5]2[S:6][C:2]1([CH3:24])[CH3:1])=[O:9])=[O:23])[CH3:33])=[O:34]

Komponenten

6

Edukt 4

HCID 6249AmpicillinHCID 516892Sodium BicarbonateHCID 30215501-Bromoethyl ethyl carbonateHCID 5462222Potassium

Produkt 1

HCID 441397Bacampicillin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A mixture of ampicillin Dane potassium salt (45.6 g), 1-bromoethyl ethyl carbonate (36.0 g), sodium bicarbonate (38.4 g) and acetonitrile (260 ml) is stirred for 3 hours at 40° C. The mixture is filtered and the cake is washed with acetonitrile (2×20 ml). Water (20 ml) is added and the mixture is stirred for 1 hour. Most of the solvent is removed by evaporation at 35°-40° C., under reduced pressure. Acetone (70 ml) and water (4.5 ml) are added. A mixture of concentrated hydrochloric acid (6.85 ml) and water (2.3 ml) is added slowly in order to keep the pH at 2-2.5. If, at the end, the pH is not stable, a small additional amount of 1:1 hydrochloric acid is added until a stable pH in the range 2-2.5 is obtained. The solution is dried and filtered. Butyl acetate (180 ml) and the solution is distilled under reduced pressure to a volume of ca. 40 ml. More butyl acetate (270 ml) is added and the product is allowed to crystallize at ca. 5° C. The mixture is filtered to give 32.5 g bacampicillin.

Aufarbeitung

  1. filtrationThe mixture is filtered
  2. washthe cake is washed with acetonitrile (2×20 ml)
  3. additionWater (20 ml) is added
  4. stirringthe mixture is stirred for 1 hour
  5. customMost of the solvent is removed by evaporation at 35°-40° C., under reduced pressure
  6. additionAcetone (70 ml) and water (4.5 ml) are added
  7. additionA mixture of concentrated hydrochloric acid (6.85 ml) and water (2.3 ml)
  8. additionis added slowly in order
  9. additiona small additional amount of 1:1 hydrochloric acid is added until a stable pH in the range 2-2.5
  10. customis obtained
  11. customThe solution is dried
  12. filtrationfiltered
  13. distillationButyl acetate (180 ml) and the solution is distilled under reduced pressure to a volume of ca. 40 ml
  14. additionMore butyl acetate (270 ml) is added
  15. customto crystallize at ca. 5° C
  16. filtrationThe mixture is filtered

Quellen und Nachweise

ORD-Eintrag
ord-2f792289a2654df2b95686dfafbf72af
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04889929

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