Water → HCID 22004859, compound

HRID 1636605Notes

Reaction equation

HRID 1636605 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 (7.32g, 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-eef8ad011c0348c59aeffd09d9ee73ae
Source dataset
uspto-grants-2000_03
Patent number
US06034239

Reaction notes

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