HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → (R)-N2-(Boc)-N5-(Cbz)-N-methyl-(R)-N-(1-phenylethyl)ornithine amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | (R)-(+)-N-Methyl-1-phenylethylamine | HCID 2060888 | — |
| Reactant | N2-((1,1-Dimethylethoxy)carbonyl)-N5-((phenylmethoxy)carbonyl)-D-ornithine | HCID 7272030 | — |
| Solvent | Acetonitrile methylene chloride | HCID 21877088 | — |
| Product | (R)-N2-(Boc)-N5-(Cbz)-N-methyl-(R)-N-(1-phenylethyl)ornithine amide | HCID 131722083 | 95.4% |
Reaction Steps
Prepared according to the method described in Example 1(a) above from Nα -Boc-Nδ -Cbz-(R)-ornithine (5.0 g; 13 mmol), BOP reagent (6.0 g; 13 mmol), HOBT (1.8 g; 13 mmol), DiPEA (7.1 mL; 40 mmol) and acetonitrile:CH2Cl2 (1:1; 100 mL) followed by (R)-(+)-N,α-dimethylbenzylamine (2.0 mL; 13 mmol), then stirred overnight. After work up the crude product was purified by chromatography on silica gel with EtOAc to provide 6.0 g (91%) of the sub-title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06127414 |
| Source dataset | uspto-grants-2000_10 |
| ORD ID | ord-afac093e37bc456fb9ac57210798b7e9 |
| Source note | uspto-grants-2000_10 |