Sodium Bicarbonate → Sulbactam

HRID 986680

반응식

HRID 986680 반응식
[CH3:1][C:2]1([CH3:17])[S:6](=[O:8])(=[O:7])[C@@H:5]2[C:9](Br)(Br)[C:10](=[O:11])[N:4]2[C@H:3]1[C:14]([OH:16])=[O:15].C(=O)(O)[O-].[Na+]>[Pd].C(OCC)(=O)C>[CH3:1][C:2]1([CH3:17])[S:6](=[O:7])(=[O:8])[C@@H:5]2[CH2:9][C:10](=[O:11])[N:4]2[C@H:3]1[C:14]([OH:16])=[O:15]

참가 물질

5

반응물 2

HCID 516892Sodium BicarbonateHCID 14277206,6-Dibromopenicillanic acid sulfone

생성물 1

HCID 130313Sulbactam수율 58%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

The ethyl acetate solution of 6,6-dibromopenicillanic acid 1,1-dioxide from Example 1 was combined with 705 ml of saturated sodium bicarbonate solution and 8.88 g of 5% palladium-on-carbon catalyst. The mixture was shaken under an atmosphere of hydrogen, at a pressure of about 5 kg/cm2 for about 1 hour. The catalyst was removed by filtration, and the pH of the aqueous phase of the filtrate was adjusted to 1.2 with 6N hydrochloric acid. The aqueous phase was saturated with sodium chloride. The layers were separated and the aqueous phase was extracted with further ethyl acetate (3×200 ml). The combined ethyl acetate solutions were dried (MgSO4) and evaporated in vacuo to afford 33.5 g (58% yield from 6-aminopenicillanic acid) of penicillanic acid 1,1-dioxide. This product was dissolved in 600 ml of ethyl acetate, the solution was decolorized using activated carbon and the solvent was removed by evaporation in vacuo. The product was washed with hexane. This afforded 31.0 g of pure product.

후처리

  1. customThe catalyst was removed by filtration
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with further ethyl acetate (3×200 ml)
  4. dry with materialThe combined ethyl acetate solutions were dried (MgSO4)
  5. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-9574147b5e1e444bb1a812bcd97436c8
출처 데이터셋
uspto-grants-1987_12
특허 번호
US04714761

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