4-(Bromomethyl)-5-methyl-1,3-dioxol-2-one → HCID 58844695, compound

HRID 1271102Notes

Reaction equation

HRID 1271102 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][CH:18]=[C:17]([CH2:21][OH:22])[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:20]=[CH:19][CH:18]=[C:17]([CH2:21][OH:22])[CH:16]=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 58844211HCID 58844211, compound

Product 1

HCID 58844695HCID 58844695, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[3-(hydroxymethyl)phenyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (160 mg) prepared by example 4 was dissolved in DMF (2.0 ml), and thereto 4-(bromomethyl)-5-methyl-1,3-dioxol-2-one (143 mg) was added at 0° C. The mixture was stirred at 0° C. for 1 hour and then thereto ice water was added. The mixture was extracted with ethyl acetate. The organic layer was washed three times with a cold saturated aqueous sodium chloride solution, followed by a cold saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by preparative thin-layer chromatography (ethyl acetate/acetone) to give (5-methyl-2-oxo-1,3-dioxo1-4-yl)methyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[3-(hydroxymethyl)phenyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (62 mg).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed three times with a cold saturated aqueous sodium chloride solution
  3. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by preparative thin-layer chromatography (ethyl acetate/acetone)

Sources & evidence

ORD record
ord-32436759016d4fa08e8c2ae6d83b42c8
Source dataset
uspto-grants-2007_04
Patent number
US07205291B2

Reaction notes

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