Acetone → HCID 178488037, compound

HRID 1192831Notes

Reaction equation

HRID 1192831 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].CC(C)([O-])C.[Na+:30].CC(C)=O>C(C(C)=O)C(C)C.CO>[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+:30]

Participants

6

Reactant 3

HCID 180AcetoneHCID 23676156Sodium t-butoxideHCID 178488147HCID 178488147, compound

Product 1

HCID 178488037HCID 178488037, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of esomeprazole (4.7 g, 13.6 mmol; 2.3% sulfone, 2.3% R-enantiomer) in methyl isobutyl ketone (30 mL) and methanol (2.1 mL) was cooled to 15° C. Sodium tert-butoxide (1.33 g, 13.8 mmol) was added in 5 min and the mixture stirred for 15 min. To the resulting solution, acetone (30 mL) was added slowly over 15 min and a solid started to crystallize. The mixture was heated to 25° C. and methyl tert-butyl ether (7.5 mL) was added dropwise. The slurry was stirred overnight. The solid was collected by filtration, rinsed with acetone (2×5 mL) and dried under reduced pressure at 50° C. to yield esomeprazole sodium. Yield: 3.2 g (65%). Sulfone content: 0.26%. R-enantiomer content: 0.01%

Workup

  1. customto crystallize
  2. additionmethyl tert-butyl ether (7.5 mL) was added dropwise
  3. stirringThe slurry was stirred overnight
  4. filtrationThe solid was collected by filtration
  5. washrinsed with acetone (2×5 mL)
  6. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-5db4d9b21a114765ac03295a7bcd0626
Source dataset
uspto-grants-2014_03
Patent number
US08680284B2

Reaction notes

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