HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzyl Chloride → Benzyl (tert-butoxycarbonyl)-L-glutaminate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzyl Chloride | HCID 7503 | — |
| Reactant | L-Glutamine, N2-((1,1-dimethylethoxy)carbonyl)- | HCID 83687 | — |
| Reactant | 3-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene | HCID 53630274 | — |
| Catalyst | Benzyl Bromide | HCID 7498 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Benzyl (tert-butoxycarbonyl)-L-glutaminate | HCID 13091521 | 59.8% |
Reaction Steps
147 g N-BOC-glutamin (t-butyloxycarbonyl-glutamin), 77 g benzylchloride and 4 g benzylbromide were refluxed in 600 ml tetrahydrofuran for 2.5 hours in the presence of a 5% excess of diazabicycloundecene. After the removal of the solvent, the residue was taken up in water-ethylacetate and washed with citric acid, sodium bicarbonate and water. Evaporating of the solvent and recrystallization from ethylacetate-hexane gave 120 g white crystals. NMR (DMSO-d6) among others: 7.36 (s,5H), 5.12 (dxd,2H), 3.989 (m,1H), 2.15 (t,2H), 1.38 (s,9H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05925339 |
| Source dataset | uspto-grants-1999_07 |
| ORD ID | ord-fe202ba6fc0b4ac895b15fe94d0f83b3 |
| Source note | uspto-grants-1999_07 |