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

HRID 2052099Notes

Reaction equation

HRID 2052099 reaction equation
BrC1C(CBr)=C(C(OC(C)(C)C)=O)N2C(=O)C(NC=O)[C@H]2S1=O.[Br:24][CH:25]1[C:30]([CH2:31][Br:32])=[C:29]([C:33]([O:35]C(C)(C)C)=[O:34])[N:28]2[C:40](=[O:52])[CH:41]([NH:42][C:43](=[O:51])[CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C@H:27]2[S:26]1=[O:53]>FC(F)(F)C(O)=O>[Br:24][CH:25]1[C:30]([CH2:31][Br:32])=[C:29]([C:33]([OH:35])=[O:34])[N:28]2[C:40](=[O:52])[CH:41]([NH:42][C:43](=[O:51])[CH2:44][C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[C@H:27]2[S:26]1=[O:53]

Participants

4

Reactant 2

HCID 70463952t-Butyl 2-bromo-3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate 1-oxideHCID 88684412t-Butyl 2-bromo-3-bromomethyl-7-formamido-3-cephem-4-carboxylate 1-oxide

Product 1

HCID 704634842-Bromo-3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylic acid 1-oxideYield 88%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The reference compound IV in the HPLC analysis was prepared as follows: 1 g (1.8 mmol) of t-butyl 2-bromo-3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate 1-oxide [prepared by the procedure of Step C of Example II] was dissolved in 15 ml of trifluoroacetic acid and after standing for 15 minutes at room temperature, the solution was evaporated to dryness. The residue was dissolved in methylene chloride and the solution was again evaporated to dryness. The residue was treated with diethyl ether and the product was isolated by filtration and was washed with diethyl ether and hexane to obtain 0.8 g (88% yield) of 2-bromo-3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylic acid 1-oxide.

Workup

  1. customthe solution was evaporated to dryness
  2. dissolutionThe residue was dissolved in methylene chloride
  3. customthe solution was again evaporated to dryness
  4. additionThe residue was treated with diethyl ether
  5. customthe product was isolated by filtration
  6. washwas washed with diethyl ether and hexane

Sources & evidence

ORD record
ord-35706c37df68464896975693e05b8575
Source dataset
uspto-grants-1980_01
Patent number
US04182870

Reaction notes

Loading…