Acetone → HCID 178488037, compound

HRID 1192833Notes

Reaction equation

HRID 1192833 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>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

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

A solution of esomeprazole (18.8 g, 54.4 mmol; 2.0% sulfone) in methyl isobutyl ketone (120 mL) was cooled to 15° C. 30% sodium methoxide in methanol (10.3 mL, 55.5 mmol) was added in 15 min. The mixture was stirred for 15 min and acetone (60 mL) was added slowly over 10 min. Subsequently, the solution was stirred at 26° C. A solid started to crystallize. After 20 min stirring, methyl tert-butyl ether (30 mL) was added dropwise. The resulting slurry was stirred overnight. 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: 14.4 g (72%). Sulfone content: 0.19%.

Workup

  1. stirringSubsequently, the solution was stirred at 26° C
  2. customto crystallize
  3. stirringAfter 20 min stirring
  4. additionmethyl tert-butyl ether (30 mL) was added dropwise
  5. stirringThe resulting slurry was stirred overnight
  6. filtrationThe solid was collected by filtration
  7. washrinsed with acetone (2×20 mL)
  8. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-aaa5f95461e84389afbf0cee79b09975
Source dataset
uspto-grants-2014_03
Patent number
US08680284B2

Reaction notes

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