4-(Bromomethyl)-5-methyl-1,3-dioxol-2-one → HCID 71045709, compound

HRID 2376670Notes

Reaction equation

HRID 2376670 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+].Br[CH2:25][C:26]1[O:27][C:28](=[O:32])[O:29][C:30]=1[CH3:31]>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][CH2:25][C:26]1[O:27][C:28](=[O:32])[O:29][C:30]=1[CH3:31])=[O:13])[CH3:3]

Participants

4

Reactant 2

HCID 107741414-(Bromomethyl)-5-methyl-1,3-dioxol-2-oneHCID 58691114HCID 58691114, compound

Product 1

HCID 71045709HCID 71045709, compoundYield 60%

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 (0.15 g) in dry DMF (2.0 ml) was ice-cooled. After 4-bromomethyl-5-methyl-1,3-dioxol-2-one (115 mg) was dropped thereto, the mixture was stirred for 30 minutes. After removal of the bath the mixture was further stirred for 30 minutes. Thereto was 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 (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-(4-methoxyphenyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.11 g, yield 60%).

Workup

  1. temperaturecooled
  2. customAfter removal of the bath the mixture
  3. stirringwas further stirred for 30 minutes
  4. washthe mixture was washed with bicarbonate solution, water and brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customthe residue was purified with silica gel column chromatography (ethyl acetate only)

Sources & evidence

ORD record
ord-934ae927db3746b3abe13d4c9dc590c9
Source dataset
uspto-grants-2008_12
Patent number
US07468364B2

Reaction notes

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