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 2052100Notes

Reaction equation

HRID 2052100 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

5.6 g 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, were dissolved in 40 ml of trifluoroacetic acid and the solution was stirred for 15 minutes at room temperature. The solvent was then evaporated, diethyl ether was added and the solvent was evaporated again. Diethyl ether was added again and the solid was filtered and dried under vacuum at room temperature to obtain 4.72 g (93.6% yield) of 2-bromo-3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylic acid 1-oxide as a pale yellow solid.

Workup

  1. customThe solvent was then evaporated
  2. additiondiethyl ether was added
  3. customthe solvent was evaporated again
  4. additionDiethyl ether was added again
  5. filtrationthe solid was filtered
  6. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-fa40b504003f4a94abcc62c0fec8d938
Source dataset
uspto-grants-1980_01
Patent number
US04182870

Reaction notes

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