HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Piperazinecarboxylic acid, ethyl ester → 4-((S)-2-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Piperazinecarboxylic acid, ethyl ester | HCID 8431 | — |
| Reactant | 5-tert-Butyl N-((phenylmethoxy)carbonyl)-L-glutamate | HCID 107472 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Tetrahydrofurane dichloromethane | HCID 21919333 | — |
| Product | 4-((S)-2-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid ethyl ester | HCID 66651778 | 98.9% |
Reaction Steps
Z-(L)Glu(OtBu)—OH (5 g), HOBT hydrate (2.5 g) and EDCI hydrochloride (3.1 g) were dissolved in DCM/THF (1/1, 42 ml). After 15 min stirring, 1-ethoxycarbonylpiperazine (2.6 g) was added and the stirring continued overnight at RT. 150 ml of EA and 60 ml of a NaHCO3 solution were added to the mixture and the phases were separated. The org. phase was washed with 60 ml of a 1M NaHSO4 solution and 60 ml of a NaCl solution, dried (Na2SO4) and evaporated off. After HV drying, 7 g of the desired compound were obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08044055B2 |
| Source dataset | uspto-grants-2011_10 |
| ORD ID | ord-4d1cedccf7dc45888bdde608c9c34029 |
| Source note | uspto-grants-2011_10 |