Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Propargyl bromide | HCID 7842 | — |
| Reactant | Diethyl 2-(benzyloxycarbonylamino)malonate | HCID 259787 | — |
| Reactant | Sodium ethoxide | HCID 2723922 | — |
| Reactant | Sodium | HCID 5360545 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 70025903 | HCID 70025903 | 41.9% |
Reaction Steps
A solution of sodium ethylate previously prepared from 500 mg of sodium in 20 ml of ethanol is added to 6 g of diethyl 2-[[(phenylmethoxy)carbonyl]amino]-propanedioate (prepared according to Bladon. C. M. J.Chem. Soc. Perkin. Trans I 9, 1151-1158 (1990) in 30 ml of ethanol then, after 30 minutes, 3 g of propargyl bromide at 80% in toluene is added and the reaction mixture is heated under reflux for 1 hour. The reaction mixture is then brought back to ambient temperature followed by evaporation under reduced pressure, taking up in dichloromethane, washing and drying. After evaporation under reduced pressure 6 g of the expected product is obtained which is purified by chromatography, eluting with a Cyclohexane/Ethyl acetate mixture 85/15. 2.82 g of purified product is obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06586442B2 |
|---|
| Source dataset | uspto-grants-2003_07 |
|---|
| ORD ID | ord-7f450d5c6e954ce29e6f4183f2a9446a |
|---|
| Source note | uspto-grants-2003_07 |
|---|