HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(4-benzyloxycarbonyl-2-oxo-1-piperazinyl)-2-[1-(tert-butoxycarbonyl)-4-piperidinyl]acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | [1-(tert-Butoxycarbonyl)piperidin-4-yl]acetic acid | HCID 1512539 | — |
| Reactant | Benzyl 4-amino-3-oxopiperazine-1-carboxylate | HCID 22727156 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | N-(4-benzyloxycarbonyl-2-oxo-1-piperazinyl)-2-[1-(tert-butoxycarbonyl)-4-piperidinyl]acetamide | HCID 22727280 | 97.9% |
Reaction Steps
A solution of 1-(tert-butoxycarbonyl)-4-piperidinylacetic acid (440 mg), 1-amino-4-benzyloxycarbonyl-2-piperazinone (541 mg), triethylamine (273 mg) and HOBt (333 mg) in DMF (30 ml) was combined with WSC (518 mg) and stirred at room temperature for 15 hours. The reaction mixture was concentrated to obtain a residue, which was partitioned between ethyl acetate and water, and the organic phase was washed with water, aqueous sodium bicarbonate, an aqueous solution of citric acid and brine, dried and concentrated to obtain N-(4-benzyloxycarbonyl-2-oxo-1-piperazinyl)-2-[1-(tert-butoxycarbonyl)-4-piperidinyl]acetamide (840 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06723722B1 |
| Source dataset | uspto-grants-2004_04 |
| ORD ID | ord-fa833f15517747bc9a31649cb8ba8585 |
| Source note | uspto-grants-2004_04 |