Sodium Hydroxide → HCID 58493968, compound

HRID 2360494Notes

Reaction equation

HRID 2360494 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])[C:8]([O:28][CH3:29])=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:27])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[C:23](OC)=[O:24])=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[C:1]([C:5]1[CH:6]=[C:7]([NH:30][S:31]([CH3:34])(=[O:32])=[O:33])[C:8]([O:28][CH3:29])=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:27])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:23][OH:24])=[O:13])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 58493979HCID 58493979, compound

Product 1

HCID 58493968HCID 58493968, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Under argon 14.7 g of methyl 2-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenylcarbamoyl)-1-methyl-1H-indole-7-carboxylate are dissolved in 120 ml of tetrahydrofuran, cooled to 0° C. and combined dropwise with 60 ml of a 1 M solution of lithium aluminium hydride in tetrahydrofuran. The mixture is stirred for 2 hours and then the reaction is stopped by the dropwise addition of 30 ml of 2 N sodium hydroxide solution. Then the mixture is stirred for 30 minutes, diluted with ethyl acetate and filtered through kieselguhr. The filter cake is taken up in 60 ml of tetrahydrofuran, stirred for 10 minutes and suction filtered through kieselguhr again. The combined organic phases are dried on magnesium sulphate and evaporated down in vacuo. The residue is extracted from methanol. The precipitated solid is filtered off and dried.

Workup

  1. stirringThen the mixture is stirred for 30 minutes
  2. filtrationfiltered through kieselguhr
  3. stirringstirred for 10 minutes
  4. filtrationsuction filtered through kieselguhr again
  5. customThe combined organic phases are dried on magnesium sulphate
  6. customevaporated down in vacuo
  7. extractionThe residue is extracted from methanol
  8. filtrationThe precipitated solid is filtered off
  9. customdried

Sources & evidence

ORD record
ord-15d7687ca5374c58be97495013efdab6
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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