Ammonia → HCID 11322604, compound

HRID 2296603Notes

Reaction equation

HRID 2296603 reaction equation
[CH3:1][C:2]1([CH3:14])S[C@@H:5]2[C@H:7]([NH2:10])[C:8](=[O:9])[N:4]2[C@H:3]1[C:11]([OH:13])=[O:12].[Mn]([O-])(=O)(=O)=O.[K+].[S:21](=[O:25])(=O)(O)[OH:22].S(=O)(O)[O-].[Na+].N>O.C(#N)C>[NH2:10][C@H:7]1[C:8](=[O:9])[N:4]2[C@@H:5]1[S:21](=[O:25])(=[O:22])[C:2]([CH3:14])([CH3:1])[C@@H:3]2[C:11]([OH:13])=[O:12]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 110826-Aminopenicillanic acidHCID 516875Potassium PermanganateHCID 23665763Sodium Bisulfite

Product 1

HCID 11322604HCID 11322604, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a 0° C. solution of 6-aminopenicillanic acid (10.0 g, 0.046 mol) in a mixture of water (32 mL) and acetonitrile(48 mL) was added, dropwise, a solution containing potassium permanganate (9.6 g, 0.061 mol) and concentrated sulfuric acid (6 mL) in water (120 mL). At the end of the addition, a 50% aqueous sodium bisulfite solution was added, dropwise, to the reaction mixture until a clear solution was observed. Anhydrous ammonia gas was passed through the solution at 0° C. until pH 3, at which time the sulfone product precipitated. The solid was filtered, washed with acetone and dried in vacuo to obtain 9.0 g(78%) of the desired product.

Workup

  1. additionwas added
  2. additionAt the end of the addition
  3. customwas passed through the solution at 0° C. until pH 3, at which time
  4. customprecipitated
  5. filtrationThe solid was filtered
  6. washwashed with acetone
  7. customdried in vacuo

Sources & evidence

ORD record
ord-13df5704c1e6473eb91893e0eeb1dd5b
Source dataset
uspto-grants-2002_12
Patent number
US06489316B2

Reaction notes

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