HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 4-[(S)-2-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoyl]-piperazine-1-carboxylic acid butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Ethylmorpholine | HCID 7525 | — |
| Reactant | O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733286 | — |
| Reactant | (S)-2-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid | HCID 66856371 | — |
| Reactant | 1-Butoxy-carbonylpiperazine | HCID 86650472 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-[(S)-2-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoyl]-piperazine-1-carboxylic acid butyl ester | HCID 66854356 | — |
Reaction Steps
To a solution of 1.6 g (S)-2-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid in 8 ml DMF were added 1.7 ml N-ethylmorpholine, 1.0 g 1-butoxy-carbonylpiperazine hydrotrifluoroacetate and 1.1 g TOTU. The solution was stirred for 12 h before being diluted with ethyl acetate and extracted subsequently with aqueous LiCl (4%), 0.1 M HCl and saturated aqueous NaHCO3. The crude product obtained after evaporation of the solvent was used without further purification. Yield: 1.8 g.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08426420B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-00fa13226e384e0288545a43d46153a9 |
| Source note | uspto-grants-2013_04 |