Sodium Bicarbonate → Sulbactam

HRID 34694

反応式

HRID 34694 の反応式
[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]

参加物

5

反応物 2

HCID 516892Sodium BicarbonateHCID 14277206,6-Dibromopenicillanic acid sulfone

生成物 1

HCID 130313Sulbactam収率 58%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-31f0a051c5024e99827cb04da651d910
出典データセット
uspto-grants-1988_08
特許番号
US04762920

関連ノート

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