Acetic Acid → HCID 86667298, compound

HRID 1261792Notes

Reaction equation

HRID 1261792 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[NH:5][CH:6]([CH3:30])[CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[C:15]([C:17]#[N:18])[CH:16]=1)[N:13]([CH2:19][CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:12][CH2:11]2)[CH3:2].OO.[OH-].[Na+].C(O)(=[O:38])C>CS(C)=O.O>[CH2:1]([O:3][C:4](=[O:31])[NH:5][CH:6]([CH3:30])[CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[C:15]([C:17](=[O:38])[NH2:18])[CH:16]=1)[N:13]([CH2:19][CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:24])[CH3:25])[CH2:12][CH2:11]2)[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 67067426HCID 67067426, compound

Product 1

HCID 86667298HCID 86667298, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
27.5 °C

Procedure

To a solution of (2-{1-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-7-cyano-2,3-dihydro-1H-indol-5-yl}-1-methyl-ethyl)-carbamic acid ethyl ester compound (V) (6 g, 0.01 mole) in DMSO (100 ml) was added 30% H2O2 (15 ml) and the mixture was stirred at 25-30° C. for 15 min. To the reaction mixture was then added 5 N NaOH solution (15 ml) and the mixture was stirred at above temperature for further period of 3 h. Acetic acid (18 ml) was added and reaction mixture was diluted with water. The mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulphate and the solvent was evaporated under reduced pressure to give 3.68 g of (VI) as pale yellow waxy solid.

Workup

  1. stirringthe mixture was stirred at above temperature for further period of 3 h
  2. customreaction mixture
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0d8e1a0d7e7b442b8ae766068450e3a7
Source dataset
uspto-grants-2013_06
Patent number
US08471039B2

Reaction notes

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