t-Butyl 2-bromo-3-bromomethyl-7-phenoxyacetamido-3-cephem-4-carboxylate-1-oxide → 2-Bromo-3-bromomethyl-7-phenoxyacetamido-3-cephem-4-carboxylic acid-1-oxide

HRID 67963Notes

Reaction equation

HRID 67963 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:30])[CH:18]([NH:19][C:20](=[O:29])[CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C@H:4]2[S:3]1=[O:31]>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:30])[CH:18]([NH:19][C:20](=[O:29])[CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C@H:4]2[S:3]1=[O:31]

Participants

3

Reactant 1

HCID 70463951t-Butyl 2-bromo-3-bromomethyl-7-phenoxyacetamido-3-cephem-4-carboxylate-1-oxide

Product 1

HCID 704638142-Bromo-3-bromomethyl-7-phenoxyacetamido-3-cephem-4-carboxylic acid-1-oxideYield 101.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1.2 g of t-butyl 2-bromo-3-bromomethyl-7-phenoxyacetamido-3-cephem-4-carboxylate-1-oxide were stirred in 8 ml of trifluoroacetic acid over 15 minutes and after evaporation to dryness under vacuo, 20 ml of 1,2-dichloroethane were added to the residue. The evaporation to dryness was repeated and 5 ml of ether and 50 ml of heptane were added to the residue. The obtained product was vacuum filtered and dried under vacuo to obtain 1.1 g of 2-bromo-3-bromomethyl-7-phenoxyacetamido-3-cephem-4-carboxylic acid-1-oxide as almost colorless crystals.

Workup

  1. customafter evaporation to dryness under vacuo, 20 ml of 1,2-dichloroethane
  2. additionwere added to the residue
  3. customThe evaporation to dryness
  4. addition5 ml of ether and 50 ml of heptane were added to the residue
  5. filtrationfiltered
  6. customdried under vacuo

Sources & evidence

ORD record
ord-ef3e67d97fc6440988185218c4b34fa1
Source dataset
uspto-grants-1982_08
Patent number
US04347358

Reaction notes

Loading…