Sodium Carbonate → HCID 14230834, compound

HRID 1759223Notes

Reaction equation

HRID 1759223 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:19](=[O:20])[N:18]2[CH:13]1[S:14][CH2:15][N:16]([C:31](=[O:33])[CH3:32])[CH:17]2[C:21]([O:23]CC1C=CC=CC=1)=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:19](=[O:20])[N:18]2[CH:13]1[S:14][CH2:15][N:16]([C:31](=[O:33])[CH3:32])[CH:17]2[C:21]([OH:23])=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 14230827HCID 14230827, compound

Product 1

HCID 14230834HCID 14230834, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled solution of benzyl 7-phenoxyacetamido-8-oxo-3-acetyl-5-thia-1,3-diazabicyclo[4,2,0]octane-2-carboxylate (300 mg.) in tetrahydrofuran (9 ml.) was added an aqueous solution (8 ml.) of sodium carbonate (107 mg.). The mixture was stirred at 0° C. for 75 minutes and at room temperature for additional 30 minutes. After removal of the tetrahydrofuran, the remaining aqueous layer was washed with ethyl acetate, acidified to pH 2 with 1 N hydrochloric acid and extracted three times with methylene chloride. Drying over magnesium sulfate and removal of the solvent gave an amorphous solid (235 mg) of 7-phenoxyacetamido-8-oxo-3-acetyl-5-thia-1,3-diazabicyclo[4,2,0]octane-2-carboxylic acid.

Workup

  1. customAfter removal of the tetrahydrofuran
  2. washthe remaining aqueous layer was washed with ethyl acetate
  3. extractionextracted three times with methylene chloride
  4. dry with materialDrying over magnesium sulfate and removal of the solvent

Sources & evidence

ORD record
ord-c0bc02ab451d4bf3bf58f0266bda89e6
Source dataset
uspto-grants-1982_07
Patent number
US04339449

Reaction notes

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