t-Butyl 7-benzamido-2-bromo-3-bromomethyl-3-cephem-4-carboxylate 1-oxide → HCID 70463170, compound

HRID 67956Notes

Reaction equation

HRID 67956 reaction equation
[C:1]([NH:9][CH:10]1[C:28](=[O:29])[N:12]2[C:13]([C:21]([O:23]C(C)(C)C)=[O:22])=[C:14]([CH2:19][Br:20])[CH:15]([Br:18])[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:28](=[O:29])[N:12]2[C:13]([C:21]([OH:23])=[O:22])=[C:14]([CH2:19][Br:20])[CH:15]([Br:18])[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 1

HCID 70462499t-Butyl 7-benzamido-2-bromo-3-bromomethyl-3-cephem-4-carboxylate 1-oxide

Product 1

HCID 70463170HCID 70463170, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 12.5 g of t-butyl 7-benzamido-2-bromo-3-bromomethyl-3-cephem-4-carboxylate-1-oxide and 50 ml of trifluoroacetic acid was stirred at room temperature for 15 minutes and was then evaporated to dryness under vacuo. 25 ml of dichloromethane were added to the residue and evaporation to dryness was repeated. A 1:1 mixture of ether and heptane was added to the residue and the formed crystals were vacuum filtered and washed with the same mixture to obtain 9.6 g of 7-benzamido-2-bromo-3-bromomethyl-3-cephem-4-carboxylic acid-1-oxide as an almost colorless solid, having the following characteristics:

Workup

  1. customwas then evaporated to dryness under vacuo
  2. addition25 ml of dichloromethane were added to the residue and evaporation to dryness
  3. additionA 1:1 mixture of ether and heptane
  4. additionwas added to the residue
  5. filtrationfiltered
  6. washwashed with the same mixture

Sources & evidence

ORD record
ord-f7f6b66003634fd1b2d1c75098283f99
Source dataset
uspto-grants-1982_08
Patent number
US04347358

Reaction notes

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