Methanol → HCID 12044464, compound
Reaction equation
[CH:1]1([CH2:6][CH:7]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[C:8]([NH:10][C:11](=[O:17])[NH:12][CH2:13][C:14]([OH:16])=[O:15])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:26]O>S(=O)(=O)(O)O.O>[CH3:26][O:15][C:14](=[O:16])[CH2:13][NH:12][C:11]([NH:10][C:8](=[O:9])[CH:7]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)[CH2:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:17]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A solution of {3-[3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-ureido}-acetic acid (30 mg, 0.08 mmol) in methanol (5 mL) was treated with concentrated sulfuric acid (4 drops). The reaction was heated to 80° C. for 8 h. At this time, the reaction was cooled to 25° C. and diluted with water (10 mL). This solution was extracted with ethyl acetate (3×20 mL). The organics were washed with a saturated aqueous sodium bicarbonate solution (1×20 mL), a saturated aqueous sodium chloride solution (1×20 mL) and water (1×10 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 80/20 hexanes/ethyl acetate) afforded {3-[3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-ureido}-acetic acid methyl ester (21 mg, 68%) as a white solid:mp 134.5-136.6° C.; EI-HRMS m/e calcd for C18H22Cl2N2O4 (M+) 400.0957, found 400.0970.
Workup
- temperatureAt this time, the reaction was cooled to 25° C.
- extractionThis solution was extracted with ethyl acetate (3×20 mL)
- washThe organics were washed with a saturated aqueous sodium bicarbonate solution (1×20 mL)
- dry with materiala saturated aqueous sodium chloride solution (1×20 mL) and water (1×10 mL), dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-ab98a58c9f71428d8270c9e71fa08e0e
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06528543B1
Reaction notes
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