Methanol → HCID 12044457, compound

HRID 1860129Notes

Reaction equation

HRID 1860129 reaction equation
CO[C:3](=[O:22])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([S:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:23][NH:24][C:25]([NH2:27])=[O:26].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][C:18]([F:21])([F:20])[F:19])=[CH:15][CH:16]=2)[C:3]([NH:27][C:25]([NH:24][CH3:23])=[O:26])=[O:22])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 4

HCID 887MethanolHCID 11719MethylureaHCID 164537Methanol, magnesium salt (2:1)HCID 462213833-Cyclopentyl-2-(4-trifluoromethylsulfanylphenyl)propionic acid methyl ester

Product 1

HCID 12044457HCID 12044457, compoundYield 18.1%

Conditions

Temperature
25 °C

Procedure

3-Cyclopentyl-2-(4-trifluoromethylsulfanyl-phenyl)propionic acid methyl ester (210.1 mg, 0.63 mmol) and methyl urea (140.5 mg, 1.90 mmol) were treated with a solution of magnesium methoxide in methanol (7.4 wt %, 3.6 mL, 2.53 mmol). The resulting reaction mixture was then heated under reflux for 64 h. The reaction mixture was allowed to cool to 25° C. and then filtered through celite. The celite was thoroughly washed with ethyl acetate until the solvent passing through the celite showed absence of desired product by thin layer chromatography. The filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 3/1 hexanes/ethyl acetate) afforded 1-[3-cyclopentyl-2-(4-trifluoromethylsulfanyl-phenyl)-propionyl]-3-methyl urea (42.7 mg, 18%) as a white solid: mp 144-145° C.; EI-HRMS m/e calcd for C17H21F3N2O2S (M+) 374.1276, found 374.1270.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas then heated
  3. temperatureunder reflux for 64 h
  4. filtrationfiltered through celite
  5. washThe celite was thoroughly washed with ethyl acetate until the solvent
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6d037e26d2b441309fd1b7dcde994e3e
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

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