Ethyl Acetate → HCID 68131608, compound

HRID 1287997Notes

Reaction equation

HRID 1287997 reaction equation
Br[CH2:2][C:3]1[CH:8]([C:9]([OH:11])=[O:10])[N:7]2[C:12](=[O:23])[CH:13]([NH:14][C:15](=[O:22])[CH2:16][C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[C@H:6]2[S:5][CH:4]=1.[C:24](=O)(O)[O-:25].[Na+].C(OCC)(=O)C>CO.C(Cl)(Cl)Cl>[CH3:24][O:25][CH2:2][C:3]1[CH:8]([C:9]([OH:11])=[O:10])[N:7]2[C:12](=[O:23])[CH:13]([NH:14][C:15](=[O:22])[CH2:16][C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[C@H:6]2[S:5][CH:4]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 68131788HCID 68131788, compound

Product 1

HCID 68131608HCID 68131608, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

The benzyl ester of 3-bromomethyl-7-(2-thienylacetamido)-2-cephem-4-carboxylic acid is dissolved in methanol. After standing at room temperature for 20 minutes the reaction mixture is poured into a dilute sodium bicarbonate solution and extracted with methylene chloride. The organic layer is washed with aqueous sodium chloride and dried. Removal of the solvent affords 35 mg. of crude product. The pure benzyl ester of 3-methoxymethyl-7-(2-thienylacetamido)-2-cephem-4-carboxylic acid is then isolated by preparative thin layer chromatography (15% ethyl acetate in chloroform as eluant).

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic layer is washed with aqueous sodium chloride
  3. customdried
  4. customRemoval of the solvent
  5. customaffords 35 mg

Sources & evidence

ORD record
ord-f94d5195e3454165a3c2c7ace22952e1
Source dataset
uspto-grants-1976_10
Patent number
US03987040

Reaction notes

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