Methanol → 1-[3-Cyclopentyl-2-(4-trifluoromethanesulfonyl-phenyl)-propionyl]-3-methyl urea
Reaction equation
CO[C:3](=[O:24])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])=[CH:13][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>>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([C:20]([F:23])([F:21])[F:22])(=[O:18])=[O:19])=[CH:13][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]1Participants
Conditions
- Temperature
- 25 °C
Procedure
3-Cyclopentyl-2-(4-trifluoromethanesulfonyl-phenyl)propionic acid methyl ester (383.8 mg, 1.05 mmol) and methyl urea (234.1 mg, 3.16 mmol) were treated with a solution of magnesium methoxide in methanol (7.4 wt %, 6.0 mL, 4.21 mmol). The resulting reaction mixture was then heated under reflux for 2 d. 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-trifluoromethanesulfonyl-phenyl)-propionyl]-3-methyl urea (119.3 mg, 28%) as a white solid: mp 191-192° C.; FAB-HRMS m/e calcd for C17H21F3N2O4S (M+H)+407.1252, found 407.1247.
Workup
- customThe resulting reaction mixture
- temperaturewas then heated
- temperatureunder reflux for 2 d
- filtrationfiltered through celite
- washThe celite was thoroughly washed with ethyl acetate until the solvent
- concentrationThe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-c68c0cf50e194f10b93f6ccf32e22162
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06528543B1
Reaction notes
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