Acetic Anhydride → HCID 12764266, compound

HRID 1580497Notes

Reaction equation

HRID 1580497 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][CH:18]=[O:19])[C:15](=[O:20])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2].C(OC(=O)C)(=O)C>N1C=CC=CC=1.CS(C)=O>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][CH:18]=[O:19])[C:15](=[O:20])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2].[C:1]([O:4][CH2:5][C:6]1[CH:11]([C:12]([OH:14])=[O:13])[N:10]2[C:15](=[O:20])[C@@H:16]([NH:17][CH:18]=[O:19])[C@H:9]2[S:8][CH:7]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 12764266HCID 12764266, compound

Product 2

HCID 12764266HCID 12764266, compoundHCID 131709931HCID 131709931, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1049PyridineSolvent

Procedure

A solution of 5 g of 3-acetyloxymethyl-7β-formylamino-ceph-3-em-4-carboxylic acid in 20 ml of pyridine and 2 ml of dimethylsulphoxide is treated with 2 ml of acetic acid anhydride and the mixture left to stand for 2 hours at room temperature. The brown reaction mixture is evaporated to dryness several times while adding absolute toluene and the residue is covered with ethyl acetate. After acidifiying with 20% aqueous phosphoric acid and saturating with sodium chloride, the layers are separated. The aqueous phase is re-extracted with ethyl acetate and the combined organic solutions are repeatedly washed with a saturated aqueous sodium chloride solution, dried over magnesium sulphate, treated with an active charcoal preparation and evaporated under reduced pressure. An approximately 1:3-mixture of 3-acetyloxymethyl-7β-formylamino-ceph-3-em-4-carboxylic acid and 3-acetyloxymethyl-7β-formylamino-ceph-2-em-4ξ-carboxylic acid is obtained, which is used without further purification.

Workup

  1. waitthe mixture left
  2. customThe brown reaction mixture is evaporated to dryness several times
  3. additionwhile adding absolute toluene
  4. concentrationsaturating with sodium chloride
  5. customthe layers are separated
  6. extractionThe aqueous phase is re-extracted with ethyl acetate
  7. washthe combined organic solutions are repeatedly washed with a saturated aqueous sodium chloride solution
  8. dry with materialdried over magnesium sulphate
  9. additiontreated with an active charcoal preparation
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-01b2bfeaac08420884c56cb77d3aed09
Source dataset
uspto-grants-1976_01
Patent number
US03932465

Reaction notes

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