Water → HCID 53761524, compound

HRID 1457273Notes

Reaction equation

HRID 1457273 reaction equation
[CH3:1][O:2][C:3]1[C:7](=[CH:8][C:9]2[NH:10][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:12][CH:13]=2)[NH:6][C:5](=[O:25])[CH:4]=1.CS(O)(=O)=O.O>C(O)CCCC.O1CCOCC1>[CH2:1]([O:2][C:3]1[C:7](=[CH:8][C:9]2[NH:10][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:12][CH:13]=2)[NH:6][C:5](=[O:25])[CH:4]=1)[CH2:7][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 3

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 54158360HCID 54158360, compound

Product 1

HCID 53761524HCID 53761524, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 62761-PentanolSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 4-methoxy-5-(5-undecyl-1H-pyrrol-2-yl-methylene)-1,5-dihydro-pyrrol-2-one (190 mg; 1 mmol) in amyl alcohol (4.75 ml) and dioxane (4.75 ml) is treated with 0.25 N methansulphonic acid in dioxane (1 ml) and stirred at room temperature under nitrogen atmosphere for 6 hours. The mixture is then poured into water (50 ml) and extracted with ethyl acetate (3×30 ml). The organic phase is shacked with brine, dried over sodium sulphate and evaporated to dryness. The crude material is purified on silica gel eluting with ethyl acetate/methanol 98/2 to give 4-amyloxy-5-(5-undecyl-1H-pyrrol-2-yl-methylene)-1,5-dihydro-pyrrol-2-one (110 mg; 0.45 mmols). Yield: 45%.

Workup

  1. extractionextracted with ethyl acetate (3×30 ml)
  2. dry with materialdried over sodium sulphate
  3. customevaporated to dryness
  4. customThe crude material is purified on silica gel eluting with ethyl acetate/methanol 98/2

Sources & evidence

ORD record
ord-c8b5ee7a2a534fa5a77d13cf70421362
Source dataset
uspto-grants-1998_12
Patent number
US05847127

Reaction notes

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