HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (R)-N2-(Boc)-N5-(Cbz)-(S)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | N2-((1,1-Dimethylethoxy)carbonyl)-N5-((phenylmethoxy)carbonyl)-D-ornithine | HCID 7272030 | — |
| Reactant | (S)-4-(1-Aminoethyl)phenol | HCID 41097924 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Solvent | Acetonitrile methylene chloride | HCID 21877088 | — |
| Product | (R)-N2-(Boc)-N5-(Cbz)-(S)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amide | HCID 86755920 | 94.8% |
Reaction Steps
Prepared according to the method described in Example 1(a) above from Nα -Boc-Nδ -Cbz-(R)-ornithine (5.34 g; 14.56 mmol), (S)-4-hydroxy-α-methylbenzylamine (2.0 g; 14.56 mmol), BOP reagent (9.67 g; 21.9 mmol), triethylamine (2.5 mL; instead of DiPEA) in acetonitrile (100 mL; instead of acetonitrile:CH2Cl2 (1:1)) to yield the sub-title compound (6.7g) as a white foam. The crude 1H NMR was consistent with the structure.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06127414 |
| Source dataset | uspto-grants-2000_10 |
| ORD ID | ord-054021804d634baeba687d8fb2c87f5b |
| Source note | uspto-grants-2000_10 |