Thioanisole → HCID 131709929, compound

HRID 1580495Notes

Reaction equation

HRID 1580495 reaction equation
[C:1]1([S:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[CH2:13][C:14]1[CH:19]([C:20]([OH:22])=[O:21])[N:18]2[C:23](=[O:34])[C@@H:24]([C:25](=[O:33])[CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@H:17]2[S:16][C:15]=1[NH2:35])(=O)C>FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>[CH3:8][S:7][C:1]1[CH:6]=[CH:5][C:4]([CH2:13][C:14]2[CH:19]([C:20]([OH:22])=[O:21])[N:18]3[C:23](=[O:34])[C@@H:24]([C:25](=[O:33])[CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C@H:17]3[S:16][C:15]=2[NH2:35])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 7520ThioanisoleHCID 131709927HCID 131709927, compound

Product 1

HCID 131709929HCID 131709929, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1.5 ml of thioanisol in 10 ml of trifluoroacetic acid is treated with 1.17 g of 3-acetyloxymethyl-7β-phenylacetyl-amino-ceph-2-em-4ξ-carboxylic acid and the mixture is left to stand for 30 minutes at room temperature. After diluting the mixture with an equal volume of toluene, the volatile fractions are evaporated under reduced pressure. The residue is partitioned between ethyl acetate and a 10% aqueous dipotassium hydrogen phosphate solution (pH = 7.5). The layers are separated; the aqueous phase is washed several times with ethyl acetate, adjusted to pH 2.5 with 20% aqueous phosphoric acid and extracted with ethyl acetate. The resulting organic extracts are washed with water and a saturated aqueous sodium chloride solution, dried over magnesium sulphate and evaporated under reduced pressure, to yield the 3-(4-methylthio-benzyl)-7β-phenylacetyl-amino-ceph-2-em-4ξ-carboxylic acid, which is further processed without purification.

Workup

  1. waitthe mixture is left
  2. customthe volatile fractions are evaporated under reduced pressure
  3. customThe residue is partitioned between ethyl acetate
  4. customThe layers are separated
  5. washthe aqueous phase is washed several times with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. washThe resulting organic extracts are washed with water
  8. dry with materiala saturated aqueous sodium chloride solution, dried over magnesium sulphate
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-82f9bd10993c4ea38bda41bcfa59eeb1
Source dataset
uspto-grants-1976_01
Patent number
US03932465

Reaction notes

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