Hydrochloric Acid → 2-(2-Carboxyfuran-5-yl-methyl)-1-(4-fluorobenzyl)-5-methanesulfonylindole

HRID 1432274Notes

Reaction equation

HRID 1432274 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]([CH2:11][C:12]2[N:13]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:16][CH:15]=3)=[CH:9][CH:10]=1)=[O:5])C.[OH-].[Li+].Cl>O1CCOCC1>[C:4]([C:6]1[O:7][C:8]([CH2:11][C:12]2[N:13]([CH2:25][C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([S:21]([CH3:24])(=[O:22])=[O:23])=[CH:16][CH:15]=3)=[CH:9][CH:10]=1)([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 225044152-(2-Ethoxycarbonylfuran-5-yl-methyl)-1-(4-fluorobenzyl)-5-methanesulfonylindole

Product 1

HCID 225044032-(2-Carboxyfuran-5-yl-methyl)-1-(4-fluorobenzyl)-5-methanesulfonylindoleYield 35.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the compound obtained in Example 30 (6) (0.003 g) in 1,4-dioxane (0.5;ml), a 10% aqueous lithium hydroxide 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 a 10% aqueous hydrochloric acid solution 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. The resulting residue was separated using silica gel preparative thin-layer chromatography (chloroform:methanol=9:1) to obtain 0.001 g of the desired product.

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
  6. customThe resulting residue was separated

Sources & evidence

ORD record
ord-1f3d2f1cd24e43bf957bd4963a20402d
Source dataset
uspto-grants-2009_11
Patent number
US07612070B2

Reaction notes

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