HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 2-Methoxycarbamoyl-piperazine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-Methylhydroxylamine hydrochloride | HCID 521874 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 4-((Benzyloxy)carbonyl)-1-((tert-butoxy)carbonyl)piperazine-2-carboxylic acid | HCID 2756778 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-Methoxycarbamoyl-piperazine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester | HCID 87321032 | — |
Reaction Steps
To a solution of piperazine-1,2,4-tricarboxylic acid 4-benzyl ester 1-tert-butyl ester (0.364 g, 1 mmol) in dichloromethane (3 mL) was added O-Methyl Hydroxylamine HCl (95 mg, 1.13 mmol), EDC HCl (0.3 g, 1.57 mmol) and DIEA (0.28 g, 2.17 mmol). The resulting mixture was stirred at room temperature overnight and partitioned between dichloromethane and water. The combined organic extracts were washed with brine, dried, and evaporated. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc/n-Hexane (30/70) to afford the title product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08399681B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-18481ddfe2264f99a312e875e5393805 |
| Source note | uspto-grants-2013_03 |