Water → HCID 10449723, compound

HRID 227494Notes

Reaction equation

HRID 227494 reaction equation
[N:1]1([S:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH:19]=C)[CH:17]=3)[NH:12][C:11]=2[C:21]([NH2:23])=[O:22])(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.I([O-])(=O)(=O)=[O:25].[Na+].O.C([O-])(O)=O.[Na+]>CC(C)=O.[Os](=O)(=O)(=O)=O>[CH:19]([C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:21]([NH2:23])=[O:22])=[C:10]2[S:7]([N:1]1[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1)(=[O:8])=[O:9])=[O:25]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 10065524HCID 10065524, compoundHCID 23667635Sodium periodate

Product 1

HCID 10449723HCID 10449723, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent

Procedure

3-(Morpholin-4-ylsulfonyl)-5-vinyl-1H-indole-2-carboxamide (207 mg, 0.617 mmol, 1.0 equiv), sodium periodate (660 mg, 3.09 mmol, 5.0 equiv) and osmium tetraoxide (16 mg, 0.062 mmol, 0.1 equiv) were dissolved in 18 mL of a 5:1 solution of acetone:water and stirred for 18 hours. The mixture was poured into aqueous saturated NaHCO3 and extracted three times with dichloromethane. The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The title compound was obtained by preparative reversed phase HPLC. Proton NMR for the product was consistent with the titled compound. ESI+MS: 338.1 [M+H]+.

Workup

  1. extractionextracted three times with dichloromethane
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1396c0bf2aec4d08901fc69f9e7238ea
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

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