Methanol → HCID 178488037, compound

HRID 1192836Notes

Reaction equation

HRID 1192836 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-].[Na+:27].CO>C(C(C)=O)C.CC(C)=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+:27]

Participants

6

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 178488147HCID 178488147, compound

Product 1

HCID 178488037HCID 178488037, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
27 °C

Procedure

A solution of esomeprazole (19.5 g, 56.5 mmol; 1.3% sulfone, 1.05% R-enantiomer) in methyl ethyl ketone (60 mL) and acetone (60 mL) was cooled to 15° C. 30% sodium methoxide in methanol (10.7 mL, 57.6 mmol) was added in 15 min. Subsequently, the solution was stirred at 27° C. A solid started to crystallize. The resulting slurry was stirred overnight at room temperature. The solid was collected by filtration, rinsed with acetone (2×20 mL) and dried under reduced pressure at 50° C. to yield esomeprazole sodium. Yield: 10.8 g (52%). Sulfone content: 0.05%. R-enantiomer content: 0.00%.

Workup

  1. customto crystallize
  2. stirringThe resulting slurry was stirred overnight at room temperature
  3. filtrationThe solid was collected by filtration
  4. washrinsed with acetone (2×20 mL)
  5. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-73b6bb94915b4d7aaeb75b39a681bccc
Source dataset
uspto-grants-2014_03
Patent number
US08680284B2

Reaction notes

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