HCID 67003370, compound → HCID 67002700, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][O:8][C:9]2([C:17]3[S:18][CH:19]=[CH:20][N:21]=3)[CH2:14][O:13]C(C)(C)[O:11][CH2:10]2)=[CH:5][CH:4]=1>CO.O.O.[Cu](Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([C:17]2[S:18][CH:19]=[CH:20][N:21]=2)([CH2:14][OH:13])[CH2:10][OH:11])=[CH:22][CH:23]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
To a solution of the 2-(5-(4-methoxybenzyloxy)-2,2-dimethyl-1,3-dioxan-5-yl)thiazole (Example 11B) (8.0 g, 23.85 mmol) in methanol (239 mL) was added copper(II) chloride dihydrate (12.20 g, 71.6 mmol) in a single portion. The mixture was heated to 70° C. for 1 hour. The reaction was cooled to room temperature and concentrated to a volume of ˜50 mL under reduced pressure. The solution was diluted with saturated aqueous ammonium chloride solution (100 mL) and ethyl acetate (150 mL). The layers were separated, and the aqueous layer was extracted with additional ethyl acetate (2×100 mL). The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound. MS ESI(+) m/z 296.3 [M+H]+.
Workup
- temperatureThe reaction was cooled to room temperature
- concentrationconcentrated to a volume of ˜50 mL under reduced pressure
- additionThe solution was diluted with saturated aqueous ammonium chloride solution (100 mL) and ethyl acetate (150 mL)
- customThe layers were separated
- extractionthe aqueous layer was extracted with additional ethyl acetate (2×100 mL)
- dry with materialThe combined organics were dried with anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-fd444cca28064787bb1693f0c6aa1cc1
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691810B2
Reaction notes
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