Omeprazole sulfide → HCID 178488147, compound

HRID 619281Notes

Reaction equation

HRID 619281 reaction equation
[CH3:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([CH3:10])[C:5]([CH2:11][S:12][C:13]2[NH:17][C:16]3[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:15]=3[N:14]=2)=[N:4][CH:3]=1.[Na].C(=O)([O-])[OH:26].[K+]>ClC1C=C(C=CC=1)C(OO)=O.O.C(Cl)Cl.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[N:4][C:5]([CH2:11][S+:12]([O-:26])[C:13]2[NH:14][C:15]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:16]=3[N:17]=2)=[C:6]([CH3:10])[C:7]=1[O:8][CH3:9]

Participants

8

Reactant 3

HCID 155794Omeprazole sulfideHCID 516893Potassium BicarbonateHCID 5360545Sodium

Product 1

HCID 178488147HCID 178488147, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent2×HCID 70297m-Chloroperbenzoic acidSolvent4×

Procedure

In step 3, m-chloroperoxybenzoic acid is dissolved in an water immiscible organic solvent such as methylene chloride or toluene. The m-chloroperoxybenzoic acid is charged to the obtained pyrmetazole in a buffered two phase system, consisting of the water immiscible solvent, such as methylene chloride or toluene, and aqueous base, such as sodium or potassium hydrogencarbonate. The organic solvent may optionally be diluted with an alcohol to enhance the solubility of the m-chloroperoxybenzoic acid. The oxidation with m-chloroperoxybenzoic acid is preferably performed between 0° and 25° C. The obtained product is extracted into an alkaline, aqueous phase and the formed product is precipitated from the aqueous phase by lowering the pH of the solution to approximately 9 at ambient temperature. Omeprazole is isolated and washed. The overall yield in the process is usually higher than 75%.

Workup

  1. customis preferably performed between 0° and 25° C
  2. extractionThe obtained product is extracted into an alkaline, aqueous phase
  3. customthe formed product is precipitated from the aqueous phase
  4. customat ambient temperature

Sources & evidence

ORD record
ord-729f1720c4274cbf80e898f9ba7c4a21
Source dataset
uspto-grants-1999_09
Patent number
US05958955

Reaction notes

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