Ethanol → HCID 178488037, compound

HRID 453673Notes

Reaction equation

HRID 453673 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]([CH2:11][S+:12]([O-:24])[C:13]2[NH:14][C:15]3[CH:16]=[CH:17][C:18]([O:22][CH3:23])=[CH:19][C:20]=3[N:21]=2)=[C:6]([CH3:10])[C:7]=1[O:8][CH3:9].C(O)C.C(OCC)(=O)C.[OH-].[Na+:35]>O>[CH3:1][C:2]1[CH:3]=[N:4][C:5]([CH2:11][S+:12]([O-:24])[C:13]2[N-:14][C:15]3[CH:16]=[CH:17][C:18]([O:22][CH3:23])=[CH:19][C:20]=3[N:21]=2)=[C:6]([CH3:10])[C:7]=1[O:8][CH3:9].[Na+:35]

Participants

6

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 178488147HCID 178488147, compound

Product 1

HCID 178488037HCID 178488037, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Esomeprazole obtained in example 14 (54.5 g; 157.78 mmol), was dissolved in a solution of aqueous NaOH (136.24 g; 4.88% w/w) and DM water (30 ml). The solution was washed with methylene chloride twice (200 ml×2). The aqueous layer was filtered and concentrated completely under reduced pressure to yield viscous mass. Ethanol was added to the viscous mass and concentrated under reduced pressure. Thereafter, ethyl acetate was added and concentrated to dryness under reduced pressure to yield solid mass. Further, ethyl acetate (400 ml) was added and stirred the mixture under reflux for 30 min. Cooled the reaction mass to 20-30° C. and stirred for 3 h. The separated solid was filtered, washed with ethyl acetate and dried under reduced pressure at 40° C. to yield esomeprazole sodium.

Workup

  1. washThe solution was washed with methylene chloride twice (200 ml×2)
  2. filtrationThe aqueous layer was filtered
  3. concentrationconcentrated completely under reduced pressure
  4. customto yield viscous mass
  5. concentrationconcentrated under reduced pressure
  6. additionThereafter, ethyl acetate was added
  7. concentrationconcentrated to dryness under reduced pressure
  8. customto yield solid mass
  9. temperatureunder reflux for 30 min
  10. stirringstirred for 3 h
  11. filtrationThe separated solid was filtered
  12. washwashed with ethyl acetate
  13. customdried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-91545b6ac3b2482c8d4a2699171439e8
Source dataset
uspto-grants-2013_07
Patent number
US08492551B2

Reaction notes

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