Methanol → HCID 178488037, compound

HRID 559273Notes

Reaction equation

HRID 559273 reaction equation
[OH-].[Na+:2].CO.[CH3:5][C:6]1[CH:7]=[N:8][C:9]([CH2:15][S+:16]([O-:28])[C:17]2[NH:18][C:19]3[CH:20]=[CH:21][C:22]([O:26][CH3:27])=[CH:23][C:24]=3[N:25]=2)=[C:10]([CH3:14])[C:11]=1[O:12][CH3:13]>C1(C)C=CC=CC=1>[CH3:5][C:6]1[CH:7]=[N:8][C:9]([CH2:15][S+:16]([O-:28])[C:17]2[N-:18][C:19]3[CH:20]=[CH:21][C:22]([O:26][CH3:27])=[CH:23][C:24]=3[N:25]=2)=[C:10]([CH3:14])[C:11]=1[O:12][CH3:13].[Na+:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 178488147HCID 178488147, compound

Product 1

HCID 178488037HCID 178488037, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.47 g of sodium hydroxide and 105 ml of methanol were taken into a round bottom flask and stirred for dissolution. 30 g of esomeprazole was taken into a separate round bottom flask and dissolved in 150 ml of toluene and this solution was added to the above sodium hydroxide solution. The combined mixture was stirred for 1.5 hours, and distilled completely at 55° C. The residue was then co-distilled with 450 ml of toluene in three equal lots. The residue was dissolved in 60 ml of toluene and stirred at 29° C. for 1 hour, 20 minutes and filtered. The solid was dried at 34° C. for 9 hours to yield 25.8 g of the title compound.

Workup

  1. stirringThe combined mixture was stirred for 1.5 hours
  2. distillationdistilled completely at 55° C
  3. dissolutionThe residue was dissolved in 60 ml of toluene
  4. stirringstirred at 29° C. for 1 hour, 20 minutes
  5. filtrationfiltered
  6. customThe solid was dried at 34° C. for 9 hours

Sources & evidence

ORD record
ord-f15d5bd33179462d8f5effa703f3c19b
Source dataset
uspto-grants-2011_11
Patent number
US08063074B2

Reaction notes

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