HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → Z-DTrp-betaAla-OEt
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | beta-Alanine, ethyl ester, hydrochloride | HCID 458475 | — |
| Reactant | N-(Benzyloxycarbonyl)-D-tryptophan | HCID 700663 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Z-DTrp-betaAla-OEt | HCID 131719105 | 72.8% |
Reaction Steps
Z-DTrp-OH (3.21 g) and βAla-OEt.HCl (1.49 g) were suspended in dichloromethane (30 ml), and N-methylmorpholine (1.05 g) and HOBT.H2O (1.59 g) were added at room temperature, and then EDCI.HCl (11.99 g) was added at 0°~5° C. The reaction mixture was stirred at room temperature overnight, diluted with dichloromethane, washed successively with sat. NaHCO3, 1N HCl and brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by dry column flash chromatography (Merck, Kieselgel 60) with dichloromethane/methanol=30/1 for elution to give the product (3.02 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05444152 |
| Source dataset | uspto-grants-1995_08 |
| ORD ID | ord-9d09d0acea554607aba452b840db75e4 |
| Source note | uspto-grants-1995_08 |