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 67961Notes

Reaction equation

HRID 67961 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:29])[CH:18]([NH:19][C:20](=[O:28])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C@H:4]2[S:3]1=[O:30]>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:29])[CH:18]([NH:19][C:20](=[O:28])[CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C@H:4]2[S:3]1=[O:30]

Participants

3

Reactant 1

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

Product 1

HCID 704634842-Bromo-3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylic acid 1-oxideYield 93.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 5.6 g of t-butyl 2-bromo-3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide in 40 ml of trifluoroacetic acid was stirred for 15 minutes at room temperature and the solvent was removed under vacuo. Ether was added to the residue, whereafter the evaporation to dryness was repeated. After addition of ether, the crystals were collected by filtration to obtain 4.72 g of 2-bromo-3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide as a slightly yellow solid having the following characteristics:

Workup

  1. customthe solvent was removed under vacuo
  2. additionEther was added to the residue, whereafter the evaporation to dryness
  3. additionAfter addition of ether
  4. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-64aac7aaf37142c7bd622460a23f19a8
Source dataset
uspto-grants-1982_08
Patent number
US04347358

Reaction notes

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