HCID 88683827, compound → 3-Bromomethyl-7-formamido-3-cephem-4-carboxylic acid-1-oxide

HRID 67958Notes

Reaction equation

HRID 67958 reaction equation
[Br:1][CH2:2][C:3]1[CH2:4][S:5](=[O:22])[C@@H:6]2[CH:17]([NH:18][CH:19]=[O:20])[C:16](=[O:21])[N:7]2[C:8]=1[C:9]([O:11]C(C)(C)C)=[O:10]>FC(F)(F)C(O)=O>[Br:1][CH2:2][C:3]1[CH2:4][S:5](=[O:22])[C@@H:6]2[CH:17]([NH:18][CH:19]=[O:20])[C:16](=[O:21])[N:7]2[C:8]=1[C:9]([OH:11])=[O:10]

Participants

3

Reactant 1

HCID 88683827HCID 88683827, compound

Product 1

HCID 884574683-Bromomethyl-7-formamido-3-cephem-4-carboxylic acid-1-oxideYield 99.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

10 g of t-butyl 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 after evaporation to dryness under vacuo, 25 ml of dichloromethane were added to the residue and evaporation to dryness was repeated. Ether was added to the residue and the formed crystals were vacuum filtered and washed with ether and the almost colorless solid was dried under vacuo to obtain 8.54 g of 3-bromomethyl-7-formamido-3-cephem-4-carboxylic acid-1-oxide having the following characteristics:

Workup

  1. customafter evaporation to dryness under vacuo, 25 ml of dichloromethane
  2. additionwere added to the residue and evaporation to dryness
  3. additionEther was added to the residue
  4. filtrationfiltered
  5. washwashed with ether
  6. customthe almost colorless solid was dried under vacuo

Sources & evidence

ORD record
ord-9745f7b052f24d179b5388d0caeaafdf
Source dataset
uspto-grants-1982_08
Patent number
US04347358

Reaction notes

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