Methanesulfonic Acid → HCID 13269670, compound

HRID 2413371Notes

Reaction equation

HRID 2413371 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13](=[O:22])[CH:14]([NH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:15])[CH:7]=[CH:6]2.[CH:23]([O-])([O-])[O:24]C.[CH3:28]S(O)(=O)=O.C(=O)(O)[O-].[Na+]>CO>[CH3:28][O:22][C:13]([O:24][CH3:23])([C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:9]=1)[CH:14]([NH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:15]

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 13269668HCID 13269668, compoundHCID 53629101Methylorthoformate

Product 1

HCID 13269670HCID 13269670, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

902 mg (3.00 mmols) of (+)-1-(6-methoxy-2-naphthyl)-2-(ethoxycarbonyl)amino-1-propanone and 6 ml of methyl orthoformate were stirred in 6 ml of anhydrous methanol at room temperature. 0.05 ml of methanesulfonic acid was added to the mixture which was then refluxed for 48 hours while stirring. The reaction mixture was cooled with ice and 20 ml of a saturated aqueous sodium bicarbonate solution was added in one portion. The mixture was extracted with methylene chloride (20 ml×2) and the extract was washed with water (20 ml×1), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The oily residue was purified by column chromatography [silica gel, ethyl acetate-hexane (1:2)] to obtain 781 mg of (+)-1-(6-methoxy-2-naphthyl)-2-(ethoxycarbonyl)amino-1-propanone dimethyl acetal as a colorless oily substance. Yield, 75%.

Workup

  1. temperaturewas then refluxed for 48 hours
  2. additionwas added in one portion
  3. extractionThe mixture was extracted with methylene chloride (20 ml×2)
  4. washthe extract was washed with water (20 ml×1)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe oily residue was purified by column chromatography [silica gel, ethyl acetate-hexane (1:2)]

Sources & evidence

ORD record
ord-10920edaa2ba4002a4cf1bdf8a55397c
Source dataset
uspto-grants-1985_01
Patent number
US04496755

Reaction notes

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