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Reaction id: 0503011027_04, verified by Personal Chemistry ©
Intermediate 10
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PS-CDI
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DMF
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Product 10
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Yield: 93% Time: 300s Temperature: 150 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| Substrate 1 |
273.318 |
1.000 |
0.500 |
136.659 mg |
| PS-CDI (0.94 mmol/g, PS) |
123.179 |
1.000 |
0.550 |
585.106 mg |
| DMF |
73.095 |
1.000 |
41.043 |
3000.000 µl |
| Product 1 |
239.238 |
1.000 |
0.500 |
119.619 mg |
Keywords
Desulfurization, Heterocyclisation, Ring closure, Ring formation, Solid phase reagent
Comments
Synthesis: PS-CDI, from Argonaut, now Biotage, was added to the crude reaction mixture containing the substrate (see 0503011015_05). Most of the solution was adsorbed on the solid supported material. The crude reaction mixture showed complete conversion and 85.7 % purity by LC-MS
Work-up: The solid supported material was filtered off and washed with 10 mL boiling acetonitrile. The solution was concentrated on rotavapor. LC-MS on the crude material showed a 87.5 % purity.
Purification: 3 mL acetone was added to the crude solid and the slurry was refluxed. After cooling to room temperature, the solid was filtered off, washed with 3 mL aceton and dried under vacuum.
Characterisation: By 1H NMR
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Coppo, F. T.; Evans, K. A.; Graybill, T. L.; Burton, G. Tetrahedron Letters 2004, 45 3257-3260
Ioannidis, P.; Lundin, R. 229th ACS National Meeting & Exposition March 13-17th, 2005, San Diego, CA
Analysis
| Method |
Purity |
Files |
| LC-MS |
100 |
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