HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Piperazinecarboxylic acid, ethyl ester → 4-((S)-4-Benzyloxy-2-tert-butoxycarbonylamino-butyryl)-piperazine-1-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Piperazinecarboxylic acid, ethyl ester | HCID 8431 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733286 | — |
| Reactant | O-Benzyl-N-(tert-butoxycarbonyl)-L-homoserine | HCID 15058464 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-((S)-4-Benzyloxy-2-tert-butoxycarbonylamino-butyryl)-piperazine-1-carboxylic acid ethyl ester | HCID 66855734 | — |
Reaction Steps
To a solution of 220 mg of (S)-4-Benzyloxy-2-tert-butoxycarbonylamino-butyric acid, 327 mg of NEM and 233 mg of TOTU in 1.6 ml of DMF, 112 mg of Piperazine-1-carboxylic acid ethyl ester was added at RT and stirred for 16 h. The reaction mixture was diluted saturated aqueous sodium hydrogen carbonate solution. After filtration through a chem Elut® cartridge by eluting with ethyl acetate the solvents were removed under reduced pressure. The isolated crude product was pure enough for the next reaction step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08669266B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-44ede83fbdd24e6c953a302ab0a9ddf1 |
| Source note | uspto-grants-2014_03 |