Ethyl Acetate → HCID 9889658, compound

HRID 1241525Notes

Reaction equation

HRID 1241525 reaction equation
[Na+].[OH:2][C@@H:3]([C@H:5]1[C:11](=[O:12])[N:10]2[C@@H:6]1[CH2:7][C:8]([C:16]1[CH:21]=[CH:20][C:19]([C:22]([NH:24][CH3:25])=[O:23])=[CH:18][CH:17]=1)=[C:9]2[C:13]([O-:15])=[O:14])[CH3:4].[C:26]([O:32][CH2:33]I)(=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28].C(OCC)(=O)C>CN(C)C=O>[OH:2][C@@H:3]([C@H:5]1[C:11](=[O:12])[N:10]2[C@@H:6]1[CH2:7][C:8]([C:16]1[CH:17]=[CH:18][C:19]([C:22]([NH:24][CH3:25])=[O:23])=[CH:20][CH:21]=1)=[C:9]2[C:13]([O:15][CH2:33][O:32][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[O:14])[CH3:4]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 104401Iodomethyl pivalateHCID 23690286HCID 23690286, compound

Product 1

HCID 9889658HCID 9889658, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-{4-[(methylamino)carbonyl]phenyl}-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid sodium salt (50 mg) in dry dimethylformamide (1 ml) was cooled with ice, and thereto was added pivaloyloxymethyl iodide (53 mg). The mixture was stirred at the same temperature for 1 hour. To the reaction solution were added ethyl acetate and ice-water, and separated. The organic layer was washed successively with a saturated brine (four times), an aqueous sodium hydrogen carbonate solution, an aqueous sodium thiosulfate solution, and a saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel thin layer chromatography (chloroform/methanol=9/1) to give [(2,2-dimethyl-propanoyl)oxy]methyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-{4-[(methylamino)carbonyl]phenyl}-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (27 mg).

Workup

  1. customseparated
  2. washThe organic layer was washed successively with a saturated brine (four times)
  3. dry with materialan aqueous sodium hydrogen carbonate solution, an aqueous sodium thiosulfate solution, and a saturated brine, and dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel thin layer chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-ea9751f974ce4cd4a175aa34abe7bc4c
Source dataset
uspto-grants-2006_10
Patent number
US07115595B2

Reaction notes

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