Sodium Bicarbonate → Sulbactam

HRID 1680826

反応式

HRID 1680826 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 Preparation K 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 6 N-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
  6. customto afford 33.5 g

出典と根拠

ORDレコード
ord-350e0132d18a4bdc951acf8c23dae5fc
出典データセット
uspto-grants-1981_06
特許番号
US04276285

関連ノート

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