Water → Sulbactam

HRID 1680822Notes

Reaction equation

HRID 1680822 reaction equation
[Mn]([O-])(=O)(=O)=[O:2].[K+].[Na].[CH3:8][C:9]1([CH3:20])[S:13][C@@H:12]2[CH2:14][C:15](=[O:16])[N:11]2[C@H:10]1[C:17]([OH:19])=[O:18].[OH2:21]>C(O)(=O)C>[CH3:8][C:9]1([CH3:20])[S:13](=[O:2])(=[O:21])[C@@H:12]2[CH2:14][C:15](=[O:16])[N:11]2[C@H:10]1[C:17]([OH:19])=[O:18]

Participants

6

Reactant 4

HCID 962Water2×HCID 6891Penicillanic AcidHCID 516875Potassium PermanganateHCID 5360545Sodium

Product 1

HCID 130313SulbactamYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 6.51 g. (41 mmole) of potassium permanganate in 130 ml. of water and 4.95 ml. of glacial acetic acid, cooled to ca. 5° C., was added a cold (ca. 5° C.) solution of 4.58 g. (21 mmole) of the sodium salt of penicillanic acid in 50 ml. of water. The mixture was stirred at ca. 5° C. for 20 minutes and then the cooling bath was removed. Solid sodium bisulfite was added until the color of the potassium permanganate had been discharged, and then the mixture was filtered. To the aqueous filtrate was added half its volume of saturated sodium chloride solution, and then the pH was adjusted to 1.7. The acidic solution was extracted with ethyl acetate. The extracts were dried, and the evaporated in vacuo, to give 3.47 g. of the title product. The aqueous mother liquor was saturated with sodium chloride, and further extracted with ethyl acetate. The ethyl acetate solution was dried and evaporated in vacuo, to give a further 0.28 g. of product. The total yield was therefore 3.75 g. (78% yield). The NMR spectrum (DMSO-d6) of the product showed absorptions at 1.40 (s, 3H), 1.50 (s, 3H), 3.13 (d of d's, 1H, J1 =16 Hz, J2 =2 Hz), 3.63 (d of d's, 1H, J1 =16 Hz, J2 =4 Hz), 4.22 (s, 1H) and 5.03 (d of d's, 1H, J1 =4 Hz, J2 =2 Hz) ppm.

Workup

  1. additionwas added a cold (ca. 5° C.) solution of 4.58 g
  2. customthe cooling bath was removed
  3. additionSolid sodium bisulfite was added until the color of the potassium permanganate
  4. filtrationthe mixture was filtered
  5. additionTo the aqueous filtrate was added half its volume of saturated sodium chloride solution
  6. extractionThe acidic solution was extracted with ethyl acetate
  7. customThe extracts were dried
  8. customthe evaporated in vacuo
  9. customto give 3.47 g

Sources & evidence

ORD record
ord-4bb6974118ff4a98836fc670a30b41ab
Source dataset
uspto-grants-1981_06
Patent number
US04276285

Reaction notes

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