Water → HCID 22004859, compound

HRID 324632Notes

Reaction equation

HRID 324632 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[CH2:8]([C:11]1[C:19]([OH:20])=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]([CH2:21][CH2:22][NH:23][C:24](=[O:27])[CH2:25][CH3:26])[CH2:14][NH:15]2)[CH:9]=[CH2:10].O>C(O)=O>[CH2:8]([C:11]1[C:19]([OH:20])=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]([CH2:21][CH2:22][NH:23][C:24](=[O:27])[CH2:25][CH3:26])[CH2:14][N:15]2[CH:1]=[O:3])[CH:9]=[CH2:10]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 22004845HCID 22004845, compound

Product 1

HCID 22004859HCID 22004859, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

Formic acid (3.3 g, 71.7 mmol) and acetic anhydride (7.32 g, 71.7 mmol) was mixed under ice-cooling and the mixture was stirred for 10 minutes. To the mixture was added a solution of N-[2-(4-allyl-2,3-dihydro-5-hydroxyindol-3-yl)ethyl]propionamide in formic acid (10 mL). The mixture was stirred for 1 hour under ice-cooling and poured into water. The product was extracted with 10% methanol/ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, brine and water, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1) to afford the title compound (yield 2.0 g, 46% from N-[2-(4-allyl-5-hydroxyindol-3-yl)ethyl]propionamide).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 1 hour under ice-
  3. temperaturecooling
  4. extractionThe product was extracted with 10% methanol/ethyl acetate
  5. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, brine and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1)

Sources & evidence

ORD record
ord-0f3b3e2ec2cb44b2a153c332e81a00a5
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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