Methanol → HCID 178488037, compound

HRID 559277Notes

Reaction equation

HRID 559277 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].ClCCl>C(#N)C>[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

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 14798Sodium Hydroxide2×HCID 178488147HCID 178488147, compound

Product 1

HCID 178488037HCID 178488037, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
29 °C

Procedure

3.47 g of sodium hydroxide and 105 ml of methanol were taken into a round bottom flask and stirred at 29° C. A solution of 30 g of esomeprazole in 150 ml of acetonitrile was added to the above methanolic sodium hydroxide solution and stirred for 1 hour at 26° C. The reaction mass was then distilled under a vacuum of 300 mm Hg at 38° C. The residue was then co-distilled with 450 ml of acetonitrile in three equal lots. To the residue obtained, 60 ml of dichloromethane was added and stirred at 29° C. for 1.5 hours. The separated solid was filtered and washed with 30 ml of acetonitrile to give 42.6 g of Form J of esomeprazole sodium.

Workup

  1. stirringstirred for 1 hour at 26° C
  2. distillationThe reaction mass was then distilled under a vacuum of 300 mm Hg at 38° C
  3. customTo the residue obtained
  4. stirringstirred at 29° C. for 1.5 hours
  5. filtrationThe separated solid was filtered
  6. washwashed with 30 ml of acetonitrile

Sources & evidence

ORD record
ord-e0a33bf81ac24313834c183b1f979e74
Source dataset
uspto-grants-2011_11
Patent number
US08063074B2

Reaction notes

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