Chloride → HCID 58691126, compound

HRID 2376668Notes

Reaction equation

HRID 2376668 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+].[Cl-].Br[CH2:26][O:27][C:28](=[O:30])[CH3:29].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][CH2:26][O:27][C:28](=[O:30])[CH3:29])=[O:13])[CH3:3]

Participants

6

Reactant 4

HCID 312ChlorideHCID 8857Ethyl AcetateHCID 68536Bromomethyl acetateHCID 58691114HCID 58691114, compound

Product 1

HCID 58691126HCID 58691126, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-(4-methoxyphenyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.18 g) in dry DMF (3.6 ml) was ice-cooled, and thereto was added triethylbenzylammoniun chloride (0.11 g). To the mixture was gradually dropped bromomethylacetate (0.16 ml) and the mixture was gradually allowed to room temperature and stirred. Forty minutes later, thereto was added ethyl acetate, 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 (ethyl acetate only) to give (acetyloxy)methyl (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 48%).

Workup

  1. temperaturecooled
  2. customwas gradually allowed to room temperature
  3. washthe mixture was washed with bicarbonate solution, water and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. customthe residue was purified with silica gel column chromatography (ethyl acetate only)

Sources & evidence

ORD record
ord-9bc9f8c64ce64682b8748d66c52bf830
Source dataset
uspto-grants-2008_12
Patent number
US07468364B2

Reaction notes

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