Methanol → HCID 178488037, compound

HRID 1192825Notes

Reaction equation

HRID 1192825 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]>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

5

Reactant 3

HCID 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 at room temperature to a solution of esomeprazole (8.5 g, 24.6 mmol; 2.2% sulfone) in methyl isobutyl ketone (60 mL). The resulting slurry was stirred overnight. The solid was collected by filtration, rinsed with methyl isobutyl ketone (2×10 mL) and dried under reduced pressure at 50° C. to yield esomeprazole sodium. Yield: 6.3 g (70%). Sulfone content: 0.33%.

Workup

  1. filtrationThe solid was collected by filtration
  2. washrinsed with methyl isobutyl ketone (2×10 mL)
  3. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-d0f7371a63724316935a3eb05b053379
Source dataset
uspto-grants-2014_03
Patent number
US08680284B2

Reaction notes

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