Sodium Hydroxide → HCID 178488041, compound

HRID 1593241Notes

Reaction equation

HRID 1593241 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]2[N:7]=[C:8]([S:10]([CH2:13][C:14]3[C:19]([CH3:20])=[C:18]([O:21][CH3:22])[C:17]([CH3:23])=[CH:16][N:15]=3)(=[O:12])=[O:11])[NH:9][C:5]=2[C:4]=1[S:26]([C:29]1[CH:40]=[CH:39][C:32]([O:33][CH2:34][C:35]([O:37]C)=[O:36])=[CH:31][CH:30]=1)(=[O:28])=[O:27].[OH-].[Na+]>C(COC)OC>[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]2[N:7]=[C:8]([S:10]([CH2:13][C:14]3[C:19]([CH3:20])=[C:18]([O:21][CH3:22])[C:17]([CH3:23])=[CH:16][N:15]=3)(=[O:12])=[O:11])[NH:9][C:5]=2[C:4]=1[S:26]([C:29]1[CH:40]=[CH:39][C:32]([O:33][CH2:34][C:35]([OH:37])=[O:36])=[CH:31][CH:30]=1)(=[O:27])=[O:28]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501786HCID 178501786, compound

Product 1

HCID 178488041HCID 178488041, compoundYield 123.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A 3L 3-necked flask equipped with a mechanical stirrer was charged with methyl 2-{4-[(5-methoxy-2-{[(4-methoxy-3,5-dimethyl(2-pyridyl))methyl]sulfonyl}benzimidazolyl)sulfonyl]phenoxy}acetate (Intermediate A27, 13.75 g, 0.024 mol) in glyme (1200 mL). To this vigorously stirring solution was added 0.1 N NaOH solution (300 mL). The resulting mixture was concentrated under reduced pressure at 47° C. The residue was triturated with fresh ethyl acetate (100 mL) for a total of four times. The residue was placed under high vacuum for 1 hr to give 17 g of a gummy solid. In a 1L 3-necked flask equipped with a mechanical stirrer was placed 16 g of this solid (equivalent to 13.3 g sodium salt, 0.0226 mol) in water (250 mL). The solution was washed by stirring with ethyl acetate (250 mL) for 1 hr and then the layers were separated. HPLC analysis of the ethyl acetate layer showed 64% omeprazole and 33% unreacted sulfoxide methyl ester. A fresh 250 mL of ethyl acetate was added to the aqueous layer. The resulting mixture was stirred and acidified to pH 3-4 with ca. 40 mL of 0.5 N hydrochloric acid. The ethyl acetate layer was separated quickly, because product started to crystallize, and placed in a freezer overnight. The crystals were collected and air dried to give 6.7 g (53%) of the methyl 2-{4-[(5-methoxy-2-{[(4-methoxy-3,5-dimethyl(2-pyridyl))methyl]sulfonyl}benzimidazolyl)sulfonyl]phenoxy}acetate.

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure at 47° C
  2. customThe residue was triturated with fresh ethyl acetate (100 mL) for a total of four times

Sources & evidence

ORD record
ord-601945d76c704f2bb10d94f09cabb9b0
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

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