Acetone → HCID 178488037, compound

HRID 1192826Notes

Reaction equation

HRID 1192826 reaction equation
C[O-].[Na+:3].CO.[CH3:6][C:7]1[CH:8]=[N:9][C:10]([CH2:16][S+:17]([O-:29])[C:18]2[NH:19][C:20]3[CH:21]=[CH:22][C:23]([O:27][CH3:28])=[CH:24][C:25]=3[N:26]=2)=[C:11]([CH3:15])[C:12]=1[O:13][CH3:14].CC(C)=O>C(C(C)=O)C(C)C>[CH3:6][C:7]1[CH:8]=[N:9][C:10]([CH2:16][S+:17]([O-:29])[C:18]2[N-:19][C:20]3[CH:21]=[CH:22][C:23]([O:27][CH3:28])=[CH:24][C:25]=3[N:26]=2)=[C:11]([CH3:15])[C:12]=1[O:13][CH3:14].[Na+:3]

Participants

6

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 10942334Sodium MethoxideHCID 178488147HCID 178488147, compound

Product 1

HCID 178488037HCID 178488037, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

30% sodium methoxide in methanol (4.7 mL, 25.3 mmol) was added dropwise to a solution of esomeprazole (8.5 g, 24.6 mmol; 2.2% sulfone, 4.7% R-enantiomer) in methyl isobutyl ketone (60 mL). The mixture was stirred for 15 min. Acetone (60 mL) was added in 30 min. The resulting slurry was stirred overnight at room temperature. The solid was collected by filtration, rinsed with acetone (2×10 mL) and dried under reduced pressure at 50° C. to yield esomeprazole sodium. Yield: 5.5 g (61%). Sulfone content: 0.17%. R-enantiomer content: 0.00%.

Workup

  1. stirringThe resulting slurry was stirred overnight at room temperature
  2. filtrationThe solid was collected by filtration
  3. washrinsed with acetone (2×10 mL)
  4. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-a0808773e4074d6f9b1449dc36fbae1a
Source dataset
uspto-grants-2014_03
Patent number
US08680284B2

Reaction notes

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