Ethyl Acetate → HCID 131713981, compound

HRID 1153783Notes

Reaction equation

HRID 1153783 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:26][O:27][CH3:28])[C:8]([NH:10][CH:11]2[C:24](=[O:25])[N:13]3[C:14]([C:21]([O-:23])=[O:22])=[C:15]([CH2:18][O:19][CH3:20])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].FC(F)(F)C([O-])=O.[C:37]([O:43][CH2:44]I)(=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39].C(OCC)(=O)C>CC(N(C)C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:26][O:27][CH3:28])[C:8]([NH:10][CH:11]2[C:24](=[O:25])[N:13]3[C:14]([C:21]([O:23][CH2:44][O:43][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])=[O:22])=[C:15]([CH2:18][O:19][CH3:20])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 84468TrifluoroacetateHCID 104401Iodomethyl pivalateHCID 131713982HCID 131713982, compound

Product 1

HCID 131713981HCID 131713981, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 45 mg of sodium 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylate (prepared from the corresponding trifluoroacetate) in 1 ml of dimethylacetamide were added, at -15° C., 27 mg of iodomethyl pivalate and the mixture was allowed to react for 15 minutes. At the end of this time, 20 ml of ethyl acetate were added to the reaction mixture, and the mixture was washed, in turn, with water, an aqueous solution of potassium bisulphate and an aqueous solution of sodium bicarbonate. The organic phase was separated and concentrated by evaporation under reduced pressure, and the residue was subjected to column chromatography through silica gel eluted with a 3:1 by volume mixture of ethyl acetate and hexane, to give 49 mg of the title compound, whose properties were identical with those of the compound obtained in Example 1.

Workup

  1. additionwere added, at -15° C.
  2. customto react for 15 minutes
  3. washthe mixture was washed, in turn, with water
  4. customThe organic phase was separated
  5. concentrationconcentrated by evaporation under reduced pressure
  6. washeluted with a 3:1 by volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-f6862b9fe121483d95770d691ef846d0
Source dataset
uspto-grants-1984_12
Patent number
US04486425

Reaction notes

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