Methanol → HCID 178488037, compound

HRID 1192837Notes

Reaction equation

HRID 1192837 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>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

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 178488147HCID 178488147, compound

Product 1

HCID 178488037HCID 178488037, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
28 °C

Procedure

A solution of esomeprazole (5.3 g, 15.3 mmol; 1.3% sulfone, 1.05% R-enantiomer) in acetone (33 mL) was cooled to 15° C. 30% sodium methoxide in methanol (2.9 mL, 15.6 mmol) was added in 15 min. Subsequently, the solution was stirred at 28° C. A solid started to crystallize. After 30 min stirring, methyl tert-butyl ether (6 mL) was added dropwise. The resulting slurry was stirred overnight at room temperature. The solid was collected by filtration, rinsed with acetone (2×6 mL) and dried under reduced pressure at 50° C. to yield esomeprazole sodium. Yield: 3.5 g (62%). Sulfone content: 0.28%. R-enantiomer content: 0.17%.

Workup

  1. customto crystallize
  2. stirringAfter 30 min stirring
  3. additionmethyl tert-butyl ether (6 mL) was added dropwise
  4. stirringThe resulting slurry was stirred overnight at room temperature
  5. filtrationThe solid was collected by filtration
  6. washrinsed with acetone (2×6 mL)
  7. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-0509cbbcb76a472ba9007e4f861d3f50
Source dataset
uspto-grants-2014_03
Patent number
US08680284B2

Reaction notes

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