Methanol → HCID 21958973, compound
Reaction equation
C[O:2][C:3](=O)[CH:4]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][C:8]2([O:15][CH2:14][CH2:13][CH2:12][O:11]2)[CH2:7]1.C[O-].[Mg+2].C[O-].CO.[NH2:32][C:33]1[S:34][CH:35]=[CH:36][N:37]=1>>[Cl:23][C:18]1[CH:17]=[C:16]([CH:4]([CH2:5][CH:6]2[CH2:10][CH2:9][C:8]3([O:11][CH2:12][CH2:13][CH2:14][O:15]3)[CH2:7]2)[C:3]([NH:32][C:33]2[S:34][CH:35]=[CH:36][N:37]=2)=[O:2])[CH:21]=[CH:20][C:19]=1[Cl:22]Participants
Conditions
- Temperature
- 25 °C
Procedure
2-(3,4-Dichloro-phenyl)-3-(6,10-dioxa-spiro[4.5]dec-2-yl)-propionic acid methyl ester (1.00 g, 2.68 mmol) was treated with a solution of magnesium methoxide in methanol (7.4 wt. % , 19 mL, 13.39 mmol), The reaction mixture was then treated with 2-aminothiazole (348.7 mg, 3.48 mmol). The resulting reaction mixture was then heated under reflux for 28 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, 230-400 mesh, 25-50% ethyl acetate/hexanes) afforded crude 2-(3,4-dichloro-phenyl)-3-(6,10-dioxa-spiro[4.5]dec-2-yl)-N-thiazol-2-yl-propionamide (768.5 mg) as a yellow oil which was used without further purification.
Workup
- customThe resulting reaction mixture
- temperaturewas then heated
- temperatureunder reflux for 28 h
- filtrationfiltered through celite
- washThe celite was thoroughly washed with ethyl acetate
- concentrationthe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-60cc264590174c57b98f7c48c13e0f30
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07259166B2
Reaction notes
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