Trifluoroacetic acid → 7-Benzamido-3-bromomethyl-3-cephem-4-carboxylic acid-1-oxide

HRID 67955Notes

Reaction equation

HRID 67955 reaction equation
[C:1]([NH:9][CH:10]1[C:27](=[O:28])[N:12]2[C:13]([C:20]([O:22]C(C)(C)C)=[O:21])=[C:14]([CH2:18][Br:19])[CH2:15][S:16](=[O:17])[C@H:11]12)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[C:1]([NH:9][CH:10]1[C:27](=[O:28])[N:12]2[C:13]([C:20]([OH:22])=[O:21])=[C:14]([CH2:18][Br:19])[CH2:15][S:16](=[O:17])[C@H:11]12)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70462724t-Butyl 7-benzamido-3-bromomethyl-3-cephem-4-carboxylate 1-oxide

Product 1

HCID 704633757-Benzamido-3-bromomethyl-3-cephem-4-carboxylic acid-1-oxideYield 104.9%

Procedure

6.25 g of t-butyl 7-benzamido-3-bromomethyl-3-cephem-4-carboxylate-1-oxide were added to 25 ml of trifluoroacetic acid at room temperature and after stirring for 15 minutes at room temperature, the trifluoroacetic acid was evaporated under vacuo. After addition of 20 ml of dichloromethane, evaporation to dryness was repeated. 25 ml of ether were added to the residue and the formed crystals were vacuum filtered, washed with ether and dried under vacuo to obtain 5.77 g of 7-benzamido-3-bromomethyl-3-cephem-4-carboxylic acid-1-oxide as a slightly yellowish colored solid having the following characteristics:

Workup

  1. customthe trifluoroacetic acid was evaporated under vacuo
  2. additionAfter addition of 20 ml of dichloromethane, evaporation to dryness
  3. addition25 ml of ether were added to the residue
  4. filtrationfiltered
  5. washwashed with ether
  6. customdried under vacuo

Sources & evidence

ORD record
ord-1d645d59cdfb44dd8bba9cbe8e0c1415
Source dataset
uspto-grants-1982_08
Patent number
US04347358

Reaction notes

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