Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | HCID 22379473 | HCID 22379473 | — |
| Reactant | HCID 54473865 | HCID 54473865 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 54006815 | HCID 54006815 | 57.6% |
Reaction Steps
To a solution of 407 mg (1.54 mmol) of (R)-3-(2, 3-methylenedioxyphenyl) octanoic acid in 8 ml of THF were added 0.24 ml of triethylamine and then 0.15 ml (1.6 mmol) of ethyl chloroformate. After stirring for 20 minutes, a solution of 264 mg (1.38 mmol) of 2, 6-diisopropylbenzylamine in tetrahydrofuran was added to the mixture, which was stirred at room temperature for 2 hours. The reaction mixture was mixed with 10 ml of water and shaken with ethyl acetate. The extract was washed with saturated saline, dried over anhydrous magnesium sulfate and the solvent evaporated in vacuo. The residue was recrystallized from a mixed solvent of hexane and ethyl acetate to give 348 mg of (R)-N-(2, 6-diisopropylbenzyl)-3-(2,3-methylenedioxyphenyl) octanamide as white crystals. Yield, 52%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05442060 |
|---|
| Source dataset | uspto-grants-1995_08 |
|---|
| ORD ID | ord-3f4546c216254a79884950c4951097b2 |
|---|
| Source note | uspto-grants-1995_08 |
|---|