Acetone → HCID 178488037, compound

HRID 1192828Notes

Reaction equation

HRID 1192828 reaction equation
CC(C)=O.[CH3:5][C:6]1[CH:7]=[N:8][C:9]([CH2:15][S+:16]([O-:28])[C:17]2[NH:18][C:19]3[CH:20]=[CH:21][C:22]([O:26][CH3:27])=[CH:23][C:24]=3[N:25]=2)=[C:10]([CH3:14])[C:11]=1[O:12][CH3:13].C[O-].[Na+:31].CO>C(C(C)=O)C(C)C>[CH3:5][C:6]1[CH:7]=[N:8][C:9]([CH2:15][S+:16]([O-:28])[C:17]2[N-:18][C:19]3[CH:20]=[CH:21][C:22]([O:26][CH3:27])=[CH:23][C:24]=3[N:25]=2)=[C:10]([CH3:14])[C:11]=1[O:12][CH3:13].[Na+:31]

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

Acetone (75 mL) was added to a solution of esomeprazole (10.1 g, 29.2 mmol; 1.1% sulfone, 2.5% R-enantiomer) in methyl isobutyl ketone (75 mL). 30% sodium methoxide in methanol (5.7 mL, 30.7 mmol) was added in 15 min. The resulting slurry was stirred overnight at room temperature. The solid was collected by filtration, rinsed with acetone (2×12 mL) and dried under reduced pressure at 50° C. to yield esomeprazole sodium. Yield: 6.5 g (61%) Sulfone content: 0.06%. R-enantiomer content: 0.00%.

Workup

  1. filtrationThe solid was collected by filtration
  2. washrinsed with acetone (2×12 mL)
  3. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-0e12a8e0baa44478a769d9040d134019
Source dataset
uspto-grants-2014_03
Patent number
US08680284B2

Reaction notes

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