Ethyl Acetate → HCID 9844859, compound

HRID 2376667Notes

Reaction equation

HRID 2376667 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[CH2:6][C:7]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)=[C:8]2[C:12]([O-:14])=[O:13])[CH3:3].[Na+].[C:24]([O:30][CH2:31]I)(=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26].C(OCC)(=O)C>CN(C=O)C>[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[CH2:6][C:7]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)=[C:8]2[C:12]([O:14][CH2:31][O:30][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[O:13])[CH3:3]

Participants

5

Reactant 3

HCID 8857Ethyl Acetate3×HCID 104401Iodomethyl pivalateHCID 58691114HCID 58691114, compound

Product 1

HCID 9844859HCID 9844859, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-(4-methoxyphenyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.17 g) was dissolved in dry DMF (1.7 ml) and the solution was ice-cooled. Thereto was gradually dropped pivaloyloxymethyl iodide (0.12 g) in dry DMF (1.2 ml) and the mixture was stirred. Thirty minutes later, ethyl acetate was added thereto and the mixture was washed with bicarbonate solution, water and brine, successively. The organic layer was dried over sodium sulfate, concentrated and the residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:2˜ethyl acetate only) to give [(2,2-dimethylpropanoyl)oxymethyl(5R,6S)-6-[(1R)-1-hydroxyethyl]-3-(4-methoxyphenyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.15 g, yield 70%).

Workup

  1. temperaturecooled
  2. washthe mixture was washed with bicarbonate solution, water and brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue was purified with silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-29b6cc9e267549f0866d05d9078d4f3c
Source dataset
uspto-grants-2008_12
Patent number
US07468364B2

Reaction notes

Loading…