Iodomethyl pivalate → HCID 18602461, compound

HRID 1381213Notes

Reaction equation

HRID 1381213 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[O:5][C:6]1[S:12][CH:11]2[N:8]([C:9](=[O:16])[C@@H:10]2[C@H:13]([OH:15])[CH3:14])[C:7]=1[C:17]([O-:19])=[O:18].[K+].[C:24]([O:30][CH2:31]I)(=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26]>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[O:5][C:6]1[S:12][CH:11]2[N:8]([C:9](=[O:16])[C@@H:10]2[C@H:13]([OH:15])[CH3:14])[C:7]=1[C:17]([O:19][CH2:31][O:30][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[O:18]

Participants

4

Reactant 2

HCID 104401Iodomethyl pivalateHCID 23700333HCID 23700333, compound

Product 1

HCID 18602461HCID 18602461, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 100 mg of potassium 3-(3-fluorophenoxy)-6(S)-{1-(R)-hydroxyethyl}-7-oxo-4-thia-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate in 1 ml of dimethylformamide were added 98 μl of pivaloyloxymethyl iodide and the mixture was stirred at room temperature for 90 minutes. The mixture was partitioned between ethyl acetate and water, the organic layer was washed with water and brine, dried over magnesium sulphate and evaporated in vacuo to dryness. Chromatography over silica gel and elution with hexane-ethylacetate afforded 50 mg of the title compound as a yellow oil.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated in vacuo to dryness
  5. washChromatography over silica gel and elution with hexane-ethylacetate

Sources & evidence

ORD record
ord-aa5d6bce3acd4c0d96476cf40f775636
Source dataset
uspto-grants-1986_04
Patent number
US04585767

Reaction notes

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