HuagongsheHuagongshe Chemistry Print Report · For research reference only
O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → (R)-N5-[Amino(nitroimino)methyl]-N2-(diphenylacetyl)-N-[[4-[(methylamino)carbonyl]-phenyl]methyl]-ornithinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | 4-Cyano-N-methylbenzamide | HCID 5080737 | — |
| Reactant | 4-(aminomethyl)-N-methylbenzamide | HCID 16777071 | — |
| Reactant | (R)-N5-[amino(nitroimino)methyl]-N2-(diphenylacetyl)-ornithine | HCID 136381100 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | (R)-N5-[Amino(nitroimino)methyl]-N2-(diphenylacetyl)-N-[[4-[(methylamino)carbonyl]-phenyl]methyl]-ornithinamide | HCID 136381111 | 22% |
Reaction Steps
Prepared, analogously to Example 67a) but using acetonitrile as solvent instead of dimethylformamide, from (R)-N5 -[amino(nitroimino)methyl]-N2 -(diphenylacetyl)-ornithine, 4-[(methylamino)carbonyl]-benzenemethylamine (prepared from 4-cyano-N-methylbenzamide by catalytic hydrogenation in the presence of palladium/animal charcoal) and TBTU in a yield of 22% of theory.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05807875 |
| Source dataset | uspto-grants-1998_09 |
| ORD ID | ord-dcb7b325a3b24a929690d1827d13ef8f |
| Source note | uspto-grants-1998_09 |