t-Butyl 2-bromo-3-bromomethyl-7-formamido-3-cephem-4-carboxylate 1-oxide → HCID 88684579, compound

HRID 67959Notes

Reaction equation

HRID 67959 reaction equation
[Br:1][CH:2]1[C:7]([CH2:8][Br:9])=[C:6]([C:10]([O:12]C(C)(C)C)=[O:11])[N:5]2[C:17](=[O:22])[CH:18]([NH:19][CH:20]=[O:21])[C@H:4]2[S:3]1=[O:23]>FC(F)(F)C(O)=O>[Br:1][CH:2]1[C:7]([CH2:8][Br:9])=[C:6]([C:10]([OH:12])=[O:11])[N:5]2[C:17](=[O:22])[CH:18]([NH:19][CH:20]=[O:21])[C@H:4]2[S:3]1=[O:23]

Participants

3

Reactant 1

HCID 88684412t-Butyl 2-bromo-3-bromomethyl-7-formamido-3-cephem-4-carboxylate 1-oxide

Product 1

HCID 88684579HCID 88684579, compoundYield 108.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

10 g of t-butyl 2-bromo-3-bromomethyl-7-formamido-3-cephem-4-carboxylate-1-oxide in 40 ml of trifluoroacetic acid were stirred for 15 minutes at room temperature and the solvent was removed by evaporation under vacuo. 25 ml of dichloromethane were added to the residue and evaporation to dryness was repeated. A 1:1 mixture of heptane and ether was added to the residue whereafter the slightly yellow crystals were vacuum filtered and were washed with the same solvent mixture to obtain 9.57 g of 2-bromo-3-bromomethyl-7-formamido-3-cephem-4-carboxylic acid-1-oxide having the following characteristics:

Workup

  1. customthe solvent was removed by evaporation under vacuo
  2. addition25 ml of dichloromethane were added to the residue and evaporation to dryness
  3. additionA 1:1 mixture of heptane and ether
  4. additionwas added to the residue whereafter the slightly yellow crystals
  5. filtrationfiltered
  6. washwere washed with the same solvent mixture

Sources & evidence

ORD record
ord-f2cae375ef234bebb4af7fd523b0058f
Source dataset
uspto-grants-1982_08
Patent number
US04347358

Reaction notes

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