Methanol → HCID 12044459, compound

HRID 1860135Notes

Reaction equation

HRID 1860135 reaction equation
CO[C:3](=[O:19])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:20][NH:21][C:22]([NH2:24])=[O:23].C[O-].[Mg+2].C[O-].CO>>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:12]=[CH:13][C:14]([S:17][CH3:18])=[CH:15][CH:16]=2)[C:3]([NH:24][C:22]([NH:21][CH3:20])=[O:23])=[O:19])[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 4

HCID 887MethanolHCID 11719MethylureaHCID 164537Methanol, magnesium salt (2:1)HCID 46221382HCID 46221382, compound

Product 1

HCID 12044459HCID 12044459, compoundYield 31%

Conditions

Temperature
25 °C

Procedure

3-Cyclopentyl-2-(4-methylsulfanyl-phenyl)propionic acid methyl ester (400 mg, 1.44 mmol) and methyl urea (267 mg, 3.60 mmol) were treated with a solution of magnesium methoxide in methanol (7.4 wt %, 5.6 mL, 3.89 mmol). The reaction mixture was then concentrated in vacuo to approximately one-half the volume of methanol. The resulting reaction mixture was then heated under reflux for 15 h. The reaction mixture was allowed to cool to 25° C., filtered through celite, and the celite was thoroughly washed with ethyl acetate. The ethyl acetate filtrate was washed with water. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 2/1 hexanes/ethyl acetate) afforded 1-[3-cyclopentyl-2-(4-methylsulfanyl-phenyl)-propionyl]-3-methyl urea (141 mg, 31%) as a white solid: mp 185-186° C.; EI-HRMS m/e calcd for C17H24N2O2S (M+) 320.1559, found 320.1559.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo to approximately one-half the volume of methanol
  2. customThe resulting reaction mixture
  3. temperaturewas then heated
  4. temperatureunder reflux for 15 h
  5. filtrationfiltered through celite
  6. washthe celite was thoroughly washed with ethyl acetate
  7. washThe ethyl acetate filtrate was washed with water
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe90611ae555430bab4beabbf9e58373
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

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