Methanol → HCID 18626605, compound

HRID 1860179Notes

Reaction equation

HRID 1860179 reaction equation
CO[C:3](=[O:24])[CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])[CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:25][NH:26][C:27]([NH2:29])=[O:28].C[O-].[Mg+2].C[O-].CO>C(OCC)(=O)C>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([S:17]([C:20]([F:21])([F:23])[F:22])(=[O:19])=[O:18])[CH:12]=2)[C:3]([NH:29][C:27]([NH:26][CH3:25])=[O:28])=[O:24])[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 887MethanolHCID 11719MethylureaHCID 164537Methanol, magnesium salt (2:1)HCID 54025663HCID 54025663, compound

Product 1

HCID 18626605HCID 18626605, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

3-Cyclopentyl-2-(3-trifluoromethanesulfonyl-phenyl)-propionic acid methyl ester (500 mg, 1.37 mmol) and methyl urea (305 mg, 4.12 mmol) were treated with a solution of magnesium methoxide in methanol (7.4 wt %, 5.9 mL, 4.12 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., diluted with ethyl acetate (10 mL), and then filtered through celite. The celite was thoroughly washed with ethyl acetate. The filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 3/1 hexanes/ethyl acetate) afforded 1-[3-cyclopentyl-2-(3-trifluoromethanesulfonyl-phenyl)-propionyl]-3-methyl-urea (253 mg, 45%) as a white foam: mp 59-62° C. (foam to gel); EI-HRMS m/e calcd for C17H21F3N2O4S (M+) 406.1174, found 406.1178.

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. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3b7e1a15c3b7434392d7ef9436a05d84
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

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