Methanol → 1-[2-(4-Bromo-phenyl)-3-cyclopentyl-propionyl]-3-methyl urea

HRID 1860126Notes

Reaction equation

HRID 1860126 reaction equation
CO[C:3](=[O:18])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:19][NH:20][C:21]([NH2:23])=[O:22].C[O-].[Mg+2].C[O-].CO>>[Br:17][C:14]1[CH:13]=[CH:12][C:11]([CH:4]([CH2:5][CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[C:3]([NH:23][C:21]([NH:20][CH3:19])=[O:22])=[O:18])=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 11719MethylureaHCID 164537Methanol, magnesium salt (2:1)HCID 462211572-(4-Bromo-phenyl)-3-cyclopentyl-propionic acid methyl ester

Product 1

HCID 120444561-[2-(4-Bromo-phenyl)-3-cyclopentyl-propionyl]-3-methyl ureaYield 12.3%

Conditions

Temperature
25 °C

Procedure

2-(4-Bromo-phenyl)-3-cyclopentyl-propionic acid methyl ester (420.0 mg, 1.35 mmol) and methyl urea (299.9 mg, 4.05 mmol) were treated with a solution of magnesium methoxide in methanol (7.4 wt %, 7.7 mL, 5.40 mmol). The resulting reaction mixture was then heated under reflux for 48 h. The reaction mixture was allowed to cool to 25° C. and then filtered through celite. The celite was thoroughly washed with ethyl acetate, and the filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 3/1 hexanes/ethyl acetate) afforded 1-[2-(4-bromo-phenyl)-3-cyclopentyl-propionyl]-3-methyl urea (58.7 mg, 12%) as a white solid: mp 184-186° C.; EI-HRMS m/e calcd for C16H21BrN2O2 (M+) 352.0786, found 352.0791.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas then heated
  3. temperatureunder reflux for 48 h
  4. filtrationfiltered through celite
  5. washThe celite was thoroughly washed with ethyl acetate
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-738adcb1446c4d29a4d9f9d78ed0f0ce
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

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