Hydrochloric Acid → 2-(2-Carboxyfuran-5-yl)-1-(4-fluorobenzyl)-5-methanesulfonyl-indole

HRID 1814118Notes

Reaction equation

HRID 1814118 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]([C:11]2[N:12]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:14]=3)=[CH:9][CH:10]=1)=[O:5])C.Cl>O1CCOCC1.[OH-].[Li+]>[C:4]([C:6]1[O:7][C:8]([C:11]2[N:12]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:14]=3)=[CH:9][CH:10]=1)([OH:5])=[O:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 225044342-(2-Ethoxycarbonylfuran-5-yl)-1-(4-fluorobenzyl)-5-methanesulfonyl-indole

Product 1

HCID 225043792-(2-Carboxyfuran-5-yl)-1-(4-fluorobenzyl)-5-methanesulfonyl-indoleYield 99.5%

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of the compound obtained in Example 29 (4) (0.0306 g) in 1,4-dioxane (0.5 ml), 10% lithium hydroxide aqueous solution (0.5 ml) was added at −5° C. under argon atmosphere and the mixture was stirred for 2 hours. To the reaction solution was then added 10% hydrochloric acid and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain 0.0285 g of the desired product as a white powder.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with a saturated aqueous NaCl solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-79d17cf75a35414581504e0422dc6542
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Reaction notes

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