Water → HCID 53761524, compound

HRID 1420865Notes

Reaction equation

HRID 1420865 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 shaken 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. stirringThe organic phase is shaken with brine
  3. dry with materialdried over sodium sulphate
  4. customevaporated to dryness
  5. customThe crude material is purified on silica gel eluting with ethyl acetate/methanol 98/2

Sources & evidence

ORD record
ord-ec2454e48cf84ff5bcc74259245d7fdc
Source dataset
uspto-grants-2000_06
Patent number
US06071947

Reaction notes

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