HuagongsheHuagongshe Chemistry Print Report · For research reference only
p-Toluenesulfonic acid → Boc-DTrp-DNle-OBzl
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | N-((tert-Butoxy)carbonyl)-D-tryptophan | HCID 111050 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | H-D-Nle-Obzl | HCID 10922067 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Boc-DTrp-DNle-OBzl | HCID 131719299 | — |
Reaction Steps
To a solution of H-DNle-OBzl.TsOH (1.27 g) in dichloromethane (20 ml) were added NMM (0.53 ml), Boc-DTrp-OH (1.22 g), HOBT.H2O (734 mg) and EDCI.HCl (926 mg) successively under ice cooling. The mixture was stirred at the same temperature for 1 h and at room temperature for 2 h. The mixture was diluted with ethyl acetate, washed with sat. aq. NaHCO3, 10% aq. citric acid, and brine successively, dried over MgSO4 and evaporated in vacuo. The residue was recrystallized from ethyl acetate and hexane to give Boc-DTrp-DNle-OBzl (1.56 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05614498 |
| Source dataset | uspto-grants-1997_03 |
| ORD ID | ord-51ab8a1120b4446597d59004935fc4b7 |
| Source note | uspto-grants-1997_03 |