Water → 1-Benzenesulfonyl-5-methanesulfonylindole-2-carboxylic acid methyl ester

HRID 1432248Notes

Reaction equation

HRID 1432248 reaction equation
COC(C1[N:6]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10](C)=[CH:9][CH:8]=2)=S.O1CCC[CH2:25]1.O.OO[S:32]([O-:34])=[O:33].[K+].[C:36]([O:39][CH2:40]C)(=[O:38])[CH3:37]>>[CH3:40][O:39][C:36]([C:37]1[N:6]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([S:32]([CH3:25])(=[O:34])=[O:33])=[CH:9][CH:8]=2)=[O:38]

Participants

6

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 23707502Potassium hydroxy sulfiteHCID 865988551-Benzenesulfonyl-5-methylthioindole-2-carboxylic acid methyl ester

Product 1

HCID 684443721-Benzenesulfonyl-5-methanesulfonylindole-2-carboxylic acid methyl ester

Conditions

Temperature
22.5 °C

Procedure

To a mixture of the compound obtained in Example 22 (1) (3.4 g), tetrahydrofuran (90 ml) and water (45 ml), OXONE (registered trademark) (8.7 g) was added at 0° C. and the mixture was stirred for 20 minutes and at 15 to 30° C. for 1 hour. The mixture was diluted with ethyl acetate. The organic layer was washed with water and dried over sodium-sulfate. The solvent was distilled off under reduced pressure to obtain 3.5 g of a white amorphous 1-benzenesulfonyl-5-methanesulfonylindole-2-carboxylic acid methyl ester as a crude product, which was used in the next reaction without; further purification.

Workup

  1. additionwas added at 0° C.
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium-sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-adb7738109f14c389c2a829559eace03
Source dataset
uspto-grants-2009_11
Patent number
US07612070B2

Reaction notes

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