Methanol → HCID 178488037, compound

HRID 1192830Notes

Reaction equation

HRID 1192830 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(C)C>[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 7909Methyl Isobutyl KetoneSolvent

Procedure

A solution of esomeprazole (9.5 g, 27.5 mmol; 2.3% sulfone, 2.3% R-enantiomer) in methyl isobutyl ketone (60 mL) was cooled to 15° C. 30% sodium methoxide in methanol (5.2 mL, 28.0 mmol) was added in 15 min. The addition funnel was rinsed with MeOH (0.3 mL) and methyl isobutyl ketone (0.7 mL). The mixture was stirred for 15 min and acetone (60 mL) was added slowly over 15 min. Subsequently, the solution was stirred at 25° C. A solid started to crystallize. After 1 h stirring, methyl tert-butyl ether (15 mL) was added dropwise. The resulting slurry was stirred overnight. The solid was collected by filtration, rinsed with acetone (2×15 mL) and dried under reduced pressure at 50° C. to yield esomeprazole sodium. Yield: 6.3 g (62%). Sulfone content: 0.23%.

Workup

  1. washThe addition funnel was rinsed with MeOH (0.3 mL) and methyl isobutyl ketone (0.7 mL)
  2. additionacetone (60 mL) was added slowly over 15 min
  3. stirringSubsequently, the solution was stirred at 25° C
  4. customto crystallize
  5. stirringAfter 1 h stirring
  6. additionmethyl tert-butyl ether (15 mL) was added dropwise
  7. stirringThe resulting slurry was stirred overnight
  8. filtrationThe solid was collected by filtration
  9. washrinsed with acetone (2×15 mL)
  10. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-2e711cb5c67749b892e85c4f0ddd2261
Source dataset
uspto-grants-2014_03
Patent number
US08680284B2

Reaction notes

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