Cesium carbonate → HCID 67525379, compound

HRID 898850Notes

Reaction equation

HRID 898850 reaction equation
[C:1]([O:5][C:6]([C@@:8]12[CH2:14][C@:13]1([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:12][O:11]C(=O)[N:9]2[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+]>CO>[C:1]([O:5][C:6]([C@@:8]1([NH:9][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:14][C@@:13]1([CH2:12][OH:11])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 67525197HCID 67525197, compound

Product 1

HCID 67525379HCID 67525379, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the obtained solution of (1R*,6R*)-3-oxo-6-phenyl-4-oxa-2-aza-bicyclo[4.1.0]heptan-1,2-dicarboxylic acid di-t-butyl ester (2.1 g, 5.5 mmol) in methanol (42 mL) was added cesium carbonate (0.54 g, 1.7 mmol) at room temperature. After stirring for 30 min., the mixture was concentrated to about half the amount under reduced pressure, and then saturated aqueous sodium chloride solution (40 mL) was added to the obtained residue. The mixture was extracted three times with ethyl acetate (30 mL), washed with water (50 mL) and saturated aqueous sodium chloride solution (50 mL), and dried over sodium sulfate. After filtration and evaporation, hexane (20 mL) was added to the obtained residue to allow precipitation of crystals. The crystals were filtrated and dried under reduced pressure to give the title compound (1.9 g, yield 74%) as a colorless amorphous form.

Workup

  1. concentrationthe mixture was concentrated to about half the amount under reduced pressure
  2. additionsaturated aqueous sodium chloride solution (40 mL) was added to the obtained residue
  3. extractionThe mixture was extracted three times with ethyl acetate (30 mL)
  4. washwashed with water (50 mL) and saturated aqueous sodium chloride solution (50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration and evaporation, hexane (20 mL)
  7. additionwas added to the obtained residue
  8. customprecipitation of crystals
  9. filtrationThe crystals were filtrated
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-0f61c961e474431cafd2e0065b8140a2
Source dataset
uspto-grants-2008_04
Patent number
US07351825B2

Reaction notes

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