Peracetic Acid → Sulbactam

HRID 224788

Reaction equation

HRID 224788 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-27f7b24ee1314ec1a204acc25be7bc42
Source dataset
uspto-grants-1980_11
Patent number
US04234579

Linked notes

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