HCID 67927934, compound → HCID 67927932, compound

HRID 1460409Notes

Reaction equation

HRID 1460409 reaction equation
C[O:2][C:3](=[O:19])[CH:4]([S:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[NH:5][C:6](=[O:10])[CH:7]([CH3:9])[CH3:8]>CO.[OH-].[Na+]>[CH2:12]([S:11][CH:4]([C:3]([OH:19])=[O:2])[NH:5][C:6](=[O:10])[CH:7]([CH3:9])[CH3:8])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 67927934HCID 67927934, compound

Product 1

HCID 67927932HCID 67927932, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Compound (3) (128.6 g; 458 mmol) in methanol (1400 ml), 1N aqueous sodium hydroxide (504 ml) was dropwise added while cooling at 0° C., and the resultant mixture was stirred at the same temperature for 1 hour and at room temperature for 3 hours, followed by concentration. The residue was diluted with a slight amount of water and washed with ether three times. The aqueous layer was collected, adjusted to pH 3 with 5% aqueous citric acid while cooling and extracted with ethyl acetate three times. The organic layer was washed with a saturated aqueous solution of sodium chloride three times, dried over anhydrous sodium sulfate and concentrated to give crude crystals. Recrystallization of said crude crystals from a mixture of ethyl acetate and petroleum ether gave Compound (4) (115.3 g; yield, 94%).

Workup

  1. concentrationfollowed by concentration
  2. additionThe residue was diluted with a slight amount of water
  3. washwashed with ether three times
  4. customThe aqueous layer was collected
  5. temperaturewhile cooling
  6. extractionextracted with ethyl acetate three times
  7. washThe organic layer was washed with a saturated aqueous solution of sodium chloride three times
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customto give crude crystals
  11. customRecrystallization
  12. additionfrom a mixture of ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-ebfaaa13e1a148d39cae2167aab1ce03
Source dataset
uspto-grants-1991_12
Patent number
US05071636

Reaction notes

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