Peracetic Acid → HCID 70479664, compound

HRID 2164401Notes

Reaction equation

HRID 2164401 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH2:10][S:11][C@@H:12]2[CH:19]([NH:20][C:21]3[NH:22][CH:23]=[CH:24][N:25]=3)[C:18](=[O:26])[N:13]2[C:14]=1[C:15]([OH:17])=[O:16].C(OO)(=O)C>C(O)(=O)C>[Cl:8][C:9]1[CH2:10][S:11][C@@H:12]2[CH:19]([NH:20][C:21]3[NH:25][CH:24]=[CH:23][N:22]=3)[C:18](=[O:26])[N:13]2[C:14]=1[C:15]([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 6585Peracetic AcidHCID 70479663HCID 70479663, compound

Product 1

HCID 70479664HCID 70479664, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-chloro-7-(imidazol-2-yl)aminocephem-4-carboxylic acid trifluoroacetate as a mixture of delta-2 and delta-3 isomers (157 mg.) in acetic acid (4 ml.) cooled to 10° was dropwise aded peracetic acid (960 μl.) The temperature was allowed to rise to ambient temperature and the mixture was stirred for 2.5 hours. The suspension was filtered to obtain a white solid (27 mg.). The filtrate was evaporated in vacuo and the residue taken up in the minimum amount of a mixture of methanol and CH2Cl2. There was thus obtained a suspension which afforded a crystalline solid on filtration. The solids were combined to give 3-chloro-7-(imidazol-2-yl)aminoceph-3-em-4-carboxylic acid as a mixture of 1α and 1β oxides (61 mg.) containing 0.17 moles of trifluoroacetic acid and having the following n.m.r. spectrum in d6 dimethyl sulphoxide+trifluoroacetic acid: 4.0 and 4.15 (s, 2H); 4.95 and 5.1 (d, 1H);5.7 and 5.8 (d, 1H); 7.05 (s, 2H).

Workup

  1. temperaturecooled to 10°
  2. customto rise to ambient temperature
  3. filtrationThe suspension was filtered
  4. customto obtain a white solid (27 mg.)
  5. customThe filtrate was evaporated in vacuo
  6. additionthe residue taken up in the minimum amount of a mixture of methanol and CH2Cl2
  7. customThere was thus obtained a suspension which
  8. customafforded a crystalline solid
  9. filtrationon filtration

Sources & evidence

ORD record
ord-8a8f4e5cedb7446593dffc57eb87aaa1
Source dataset
uspto-grants-1985_03
Patent number
US04504478

Reaction notes

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