HCID 70195797, compound → 3-Bromomethyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide

HRID 67962Notes

Reaction equation

HRID 67962 reaction equation
[Br:1][CH2:2][C:3]1[CH2:4][S:5](=[O:29])[C@@H:6]2[CH:17]([NH:18][C:19](=[O:27])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:16](=[O:28])[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:29])[C@@H:6]2[CH:17]([NH:18][C:19](=[O:27])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:16](=[O:28])[N:7]2[C:8]=1[C:9]([OH:11])=[O:10]

Participants

3

Reactant 1

HCID 70195797HCID 70195797, compound

Product 1

HCID 679284423-Bromomethyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxideYield 102.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 37.3 g of t-butyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide in 130 ml of trifluoroacetic acid was stirred for 15 minutes at room temperature and then the solvent was removed by evaporation under vacuo. After addition of 100 ml of 1,2-dichloroethane, evaporation to dryness was repeated. Ether was added to the residue and the crystals were vacuum filtered, washed with ether and dried under vacuo to obtain 33.7 g of 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide as an almost colorless solid having the following characteristics:

Workup

  1. customthe solvent was removed by evaporation under vacuo
  2. additionAfter addition of 100 ml of 1,2-dichloroethane, evaporation to dryness
  3. additionEther was added to the residue
  4. filtrationfiltered
  5. washwashed with ether
  6. customdried under vacuo

Sources & evidence

ORD record
ord-dec68ae2819140e6b643d81d63ad9589
Source dataset
uspto-grants-1982_08
Patent number
US04347358

Reaction notes

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