Sodium Hydroxide → HCID 178488038, compound

HRID 1593231Notes

Reaction equation

HRID 1593231 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]2[N:7]=[C:8]([S:10]([CH2:12][C:13]3[C:18]([CH3:19])=[C:17]([O:20][CH3:21])[C:16]([CH3:22])=[CH:15][N:14]=3)=[O:11])[NH:9][C:5]=2[C:4]=1[S:25]([C:28]1[C:39]([CH3:40])=[CH:38][C:31]([O:32][CH2:33][C:34]([O:36]C)=[O:35])=[CH:30][C:29]=1[CH3:41])(=[O:27])=[O:26].[OH-].[Na+:43]>C(COC)OC>[Na+:43].[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]2[N:7]=[C:8]([S:10]([CH2:12][C:13]3[C:18]([CH3:19])=[C:17]([O:20][CH3:21])[C:16]([CH3:22])=[CH:15][N:14]=3)=[O:11])[NH:9][C:5]=2[C:4]=1[S:25]([C:28]1[C:29]([CH3:41])=[CH:30][C:31]([O:32][CH2:33][C:34]([O-:36])=[O:35])=[CH:38][C:39]=1[CH3:40])(=[O:26])=[O:27]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501781HCID 178501781, compound2×

Product 1

HCID 178488038HCID 178488038, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of methyl {4-[(5-methoxy-2{[4-methoxy,3,5-dimethyl(2-pyridyl)methyl]sulfinyl}benzimidazolyl)sulfonyl]-3,5-dimethylphenoxy}acetate (Intermediate A6, 2.96 g, 0.493 mol) in 250 mL of dimethoxyethane was stirred rapidly as 49 mL of 0.100 N aqueous sodium hydroxide was added. The mixture was concentrated at aspirator pressure (bath temperature<22° C.). The residue was reconcentrated from 200 mL of dimethoxyethane, left briefly at high vacuum, and partitioned between ethyl acetate and water. The aqueous layer was washed with several portions of ethyl acetate and was then concentrated at high vacuum. The residue was partitioned between ethyl acetate and water at pH 3. The aqueous layer was extracted with an additional portion of ethyl acetate, and the combined organic layers were reduced in volume and diluted with hexanes. The resulting solid was collected and combined with a second crop recovered from the filtrate. This material was washed with 10:1 diethyl ether:tetrahydrofuran, dissolved in dimethoxyethane, neutralized with 0.0100 N sodium hydroxide, and washed with ethyl acetate. The product, title compound weighed 0.925 g (31%).

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated at aspirator pressure (bath temperature<22° C.)
  3. waitleft briefly at high vacuum
  4. custompartitioned between ethyl acetate and water
  5. washThe aqueous layer was washed with several portions of ethyl acetate
  6. concentrationwas then concentrated at high vacuum
  7. customThe residue was partitioned between ethyl acetate and water at pH 3
  8. extractionThe aqueous layer was extracted with an additional portion of ethyl acetate
  9. additiondiluted with hexanes
  10. customThe resulting solid was collected
  11. customrecovered from the filtrate
  12. washThis material was washed with 10:1 diethyl ether
  13. dissolutiontetrahydrofuran, dissolved in dimethoxyethane
  14. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-99beeb4a23784e80b7b3a993838a2ebd
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

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