HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (5-[1-(t-Butyldimethylsiloxy)vinyl]-3-{[2-(4-fluorophenyl)ethyl]-methylsulfamoyl}thiophene-2-yl)carbamic acid t-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | tert-Butyldimethylsilyl trifluoromethanesulphonate | HCID 123564 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | (5-Acetyl-3-{[2-(4-fluorophenyl)ethyl]methylsulfamoyl}thiophene-2-yl)-carbamic acid t-butyl ester | HCID 69414947 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (5-[1-(t-Butyldimethylsiloxy)vinyl]-3-{[2-(4-fluorophenyl)ethyl]-methylsulfamoyl}thiophene-2-yl)carbamic acid t-butyl ester | HCID 69415031 | — |
Reaction Steps
To a solution of (5-acetyl-3-{[2-(4-fluorophenyl)ethyl]methylsulfamoyl}thiophene-2-yl)-carbamic acid t-butyl ester (the compound of Preparation Example 111) (946 mg) in dichloromethane (8 mL) was added triethylamine (0.58 mL) and 0.71 mL of t-butyldimethylsilyltrifluoromethane sulfonate (0.71 mL) on an ice bath. After stirring for 30 minutes, an aqueous solution of saturated sodium bicarbonate was added, and the solution was extracted with ethyl acetate. After drying the organic layer with anhydrous sodium sulfate, the residue that was obtained upon removal of the solvent by evaporation was purified by silica gel column chromatography (hexane/ethyl acetate) and, the title compound (985 mg) was obtained as a colorless oily matter.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07217723B2 |
| Source dataset | uspto-grants-2007_05 |
| ORD ID | ord-ee232449073445d9ad25b1a320fd3590 |
| Source note | uspto-grants-2007_05 |