HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → Ethyl 3-[3-[(tert-butoxycarbonyl)amino]-4-(2-{4-[(methylsulfonyl)oxy]phenyl}ethoxy)phenyl]-2-ethoxypropanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-(Methylsulfonyloxy)-2-[4-(methylsulfonyloxy)phenyl]ethane | HCID 11220122 | — |
| Reactant | HCID 22708408 | HCID 22708408 | — |
| Solvent | Methyl Ethyl Ketone | HCID 6569 | — |
| Product | Ethyl 3-[3-[(tert-butoxycarbonyl)amino]-4-(2-{4-[(methylsulfonyl)oxy]phenyl}ethoxy)phenyl]-2-ethoxypropanoate | HCID 22708435 | 21.4% |
Reaction Steps
Ethyl 3-{3-[(tert-butoxycarbonyl)amino]-4-hydroxyphenyl}-2-ethoxypropanoate (0.16 g, 0.44 mmole) and 4-{2-[(methylsulfonyl)oxy]ethyl}phenyl methanesulfonate (0.26 g, 0.88 mmole) were dissolved in 2-butanone (10 ml). Polyethyleneglycol 400 (0.05 g) and anhydrous potassium carbonate (0.092 g, 0.66 mmole) were added the mixture. After stirring at reflux for 16 hours it was checked with using HPLC whether all the starting material was consumed. The mixture was washed with water dried with magnesium sulfate and evaporated. Purification of the crude product with preparative HPLC (Kromasil C8, 7 μm, 50×250 mm) using actonitrile(60-80%) in ammonium acetate buffer (pH 7) as mobile phase gave 0.052 g (21% yield) of the desired product
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06750252B2 |
| Source dataset | uspto-grants-2004_06 |
| ORD ID | ord-b30695ede53f4abbae1e28d66ba39090 |
| Source note | uspto-grants-2004_06 |