Ampicillin → Bacampicillin

HRID 478050

반응식

HRID 478050 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 441397Bacampicillin

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2f792289a2654df2b95686dfafbf72af
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04889929

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