Potassium thiocyanate → 3-Carbamoyloxymethyl-7-(3-oxo-4-thiocyanatobutyramido)-3-cephem-4-carboxylic acid

HRID 127112Notes

Reaction equation

HRID 127112 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:24])[CH2:19][C:20](=[O:23])[CH2:21]Br)[C:15](=[O:25])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[NH2:2].[S-:26][C:27]#[N:28].[K+]>C(#N)C>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:24])[CH2:19][C:20](=[O:23])[CH2:21][S:26][C:27]#[N:28])[C:15](=[O:25])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 516872Potassium thiocyanateHCID 886069703-Carbamoyloxymethyl-7-(3-oxo-4-bromobutyramido)-3-cephem-4-carboxylic acid

Product 1

HCID 1317121113-Carbamoyloxymethyl-7-(3-oxo-4-thiocyanatobutyramido)-3-cephem-4-carboxylic acidYield 72.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-carbamoyloxymethyl-7-(3-oxo-4-bromobutyramido)-3-cephem-4-carboxylic acid (0.52 g.) and potassium thiocyanate (0.174 g.) in acetonitrile (10 ml.) was stirred for 6 hours at room temperature, and then acetonitrile was distilled off therefrom. To the residue were added ethyl acetate (50 ml.) and a saturated aqueous solution of sodium chloride (20 ml.), and the mixture was adjusted to pH 2 with 50% phosphoric acid with stirring, and then ethyl acetate layer was separated therefrom. The remaining aqueous layer was further extracted with ethyl acetate. The ethyl acetate layers were combined together, dried over magnesium sulfate, treated with activated carbon, and then the solvent was distilled off therefrom. The residue was pulverized in diethyl ether, collected by filtration and then dried to give 3-carbamoyloxymethyl-7-(3-oxo-4-thiocyanatobutyramido)-3-cephem-4-carboxylic acid (0.36 g.).

Workup

  1. distillationacetonitrile was distilled off
  2. additionTo the residue were added ethyl acetate (50 ml.)
  3. stirringwith stirring
  4. customethyl acetate layer was separated
  5. extractionThe remaining aqueous layer was further extracted with ethyl acetate
  6. dry with materialdried over magnesium sulfate
  7. additiontreated with activated carbon
  8. distillationthe solvent was distilled off
  9. filtrationcollected by filtration
  10. customdried

Sources & evidence

ORD record
ord-c1b76f7a9b764f69b70599d486d49fdd
Source dataset
uspto-grants-1981_03
Patent number
US04254260

Reaction notes

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