Peracetic Acid → Sulbactam

HRID 1680825Notes

Reaction equation

HRID 1680825 reaction equation
[CH3:1][C:2]1([CH3:13])S[C@@H:5]2[CH2:7][C:8](=[O:9])[N:4]2[C@H:3]1[C:10]([OH:12])=[O:11].C(OO)(=O)C.[S:19](=[O:22])(O)[O-:20].[Na+]>O.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:13])[S:19](=[O:22])(=[O:20])[C@@H:5]2[CH2:7][C:8](=[O:9])[N:4]2[C@H:3]1[C:10]([OH:12])=[O:11]

Participants

6

Reactant 3

HCID 6585Peracetic Acid2×HCID 6891Penicillanic AcidHCID 23665763Sodium Bisulfite

Product 1

HCID 130313Sulbactam

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1.78 g. of penicillanic acid in water, at pH 7.5, was added 1.46 ml. of 40% peracetic acid, followed by an additional 2.94 ml. of 40% peracetic acid 30 minutes later. The reaction mixture was stirred for 3 days at room temperature and then it was diluted with ethyl acetate and water. Solid sodium bisulfite was added to decompose excess peracid, and then the pH was adjusted to 1.5. The ethyl acetate layer was removed, dried (Na2SO4) and evaporated in vacuo. The residue was a 3:2 mixture of penicillanic acid 1,1-dioxide and penicillanic acid 1-oxide.

Workup

  1. customThe ethyl acetate layer was removed
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo
  4. additiona 3:2 mixture of penicillanic acid 1,1-dioxide and penicillanic acid 1-oxide

Sources & evidence

ORD record
ord-ec5f1d24152b455ea93d182dc58a78e2
Source dataset
uspto-grants-1981_06
Patent number
US04276285

Reaction notes

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