HuagongsheHuagongshe Chemistry Print Report · For research reference only
Carzenide → Tert-butyl (cis)-3-{[4-(aminosulfonyl)benzoyl]amino}-4-{[(benzyloxy)carbonyl]amino}-1-piperidinecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Carzenide | HCID 8739 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | tert-Butyl 3-amino-4-(((benzyloxy)carbonyl)amino)piperidine-1-carboxylate | HCID 22143118 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Tert-butyl (cis)-3-{[4-(aminosulfonyl)benzoyl]amino}-4-{[(benzyloxy)carbonyl]amino}-1-piperidinecarboxylate | HCID 86587040 | 45.9% |
Reaction Steps
1-tert-butoxycarbonyl-3-amino-4-(benzyloxycarbonyl)amino-piperidine (151b) (300 mg) was dissolved in DMF (5 mL) prior to addition of Hunig's base (0.45 mL). 4-(aminosulfonyl)benzoic acid (210 mg) was added followed by BOP (420 mg). The solution was stirred for 8 h then quenched with aqueous NH4Cl. The mixture was partitioned between EtOAc and water. The organic layer was washed with NaHCO3, 5% LiCl (3×), and brine. The organic layer was dried, filtered, and concentrated. Flash chromatography of the residue provided tert-butyl (cis)-3-{[4-(aminosulfonyl)benzoyl]amino}-4-{[(benzyloxy)carbonyl]amino}-1-piperidinecarboxylate (210 mg). MS found: (M−H)−=531.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07045521B2 |
| Source dataset | uspto-grants-2006_05 |
| ORD ID | ord-ba88124e1e694a01900adf8968c55647 |
| Source note | uspto-grants-2006_05 |