Hydrochloric Acid → 6,6-Dibromopenicillanic acid sulfone

HRID 1680828

반응식

HRID 1680828 반응식
[CH3:1][C:2]1([CH3:15])S[C@@H:5]2[C:7]([Br:11])([Br:10])[C:8](=[O:9])[N:4]2[C@H:3]1[C:12]([OH:14])=[O:13].[OH-].[Na+].[Mn]([O-])(=O)(=O)=O.[K+].P(=O)(O)(O)O.[Mn]([O-])(=O)(=O)=O.Cl.[S:35](=[O:38])(O)[O-:36].[Na+].[Cl-].[Na+]>C(OCC)(=O)C.O.ClCCl>[CH3:1][C:2]1([CH3:15])[S:35](=[O:38])(=[O:36])[C@@H:5]2[C:7]([Br:10])([Br:11])[C:8](=[O:9])[N:4]2[C@H:3]1[C:12]([OH:14])=[O:13]

참가 물질

12

반응물 8

HCID 313Hydrochloric Acid2회HCID 1004Phosphoric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 24401PermanganateHCID 903766,6-Dibromopenicillanic acidHCID 516875Potassium PermanganateHCID 23665763Sodium Bisulfite2회

생성물 1

HCID 14277206,6-Dibromopenicillanic acid sulfone

시약·촉매·용매 3

HCID 962Water용매2회HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To the dichloromethane solution of 6,6-dibromopenicillanic acid from Preparation J was added 300 ml. of water, followed by the dropwise addition over a period of 30 minutes of 105 ml. of 3 N sodium hydroxide. The pH stabilized at 7.0. The aqueous layer was removed and the organic layer was extracted with water (2×100 ml.). To the combined aqueous solutions was added, at -5° C., a premixed solution prepared from 59.25 g. of potassium permanganate, 18 ml. of concentrated phosphoric acid and 600 ml. of water, until the pink color of the permanganate persisted. The addition took 50 minutes and 500 ml. of oxidant were required. At this point, 500 ml. of ethyl acetate was added and then the pH was lowered to 1.23 by the addition of 105 ml. of 6 N hydrochloric acid. Then 250 ml. of 1 M sodium bisulfite was added during 10-15 minutes at ca. 10° C. During the addition of the sodium bisulfite solution, the pH was maintained at 1.25-1.35 using 6 N hydrochloric acid. The aqueous phase was saturated with sodium chloride and the two phases were separated. The aqueous solution was extracted with additional ethyl acetate (2×150 ml.) and the combined ethyl acetate solutions were washed with brine and dried (MgSO4). This afforded an ethyl acetate solution of 6,6-dibromopenicillanic acid 1,1-dioxide.

후처리

  1. additionwas added 300 ml
  2. customThe aqueous layer was removed
  3. extractionthe organic layer was extracted with water (2×100 ml.)
  4. additionTo the combined aqueous solutions was added, at -5° C.
  5. customa premixed solution prepared from 59.25 g
  6. additionThe addition
  7. additionthe pH was lowered to 1.23 by the addition of 105 ml
  8. customthe two phases were separated
  9. extractionThe aqueous solution was extracted with additional ethyl acetate (2×150 ml.)
  10. washthe combined ethyl acetate solutions were washed with brine
  11. dry with materialdried (MgSO4)

출처 및 근거

ORD 기록
ord-b3987dc640d24eb4adcb974efdfa19c9
출처 데이터셋
uspto-grants-1981_06
특허 번호
US04276285

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