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 | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 5-tert-Butyl N-((phenylmethoxy)carbonyl)-L-glutamate | HCID 107472 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| 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
To a solution of Z-(L)Glu(OtBu)-OH (5 g) in DCM/THF (1:1, 42 ml) were added at RT HOBT (2.5 g) and EDCI (3.1 g). After 15 min stirring at RT, 1-ethoxycarbonylpiperazine (2.6 g) was added and the stirring was continued at RT overnight. 150 ml of EA and 60 ml of a NaHCO3 solution were added to the reaction mixture and the phases were separated. The org. phase was washed with an aq. NaHSO4 (1M) solution and with brine, dried over 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 | US08093250B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-ab5337ab9c34419089794c0202e6fccf |
| Source note | uspto-grants-2012_01 |