HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (S)-tert-Butyl (3-(benzyloxy)-1-(5-bromo-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Bromine | HCID 24408 | — |
| Reactant | Sodium methanethiolate | HCID 4378561 | — |
| Reactant | (S)-tert-Butyl (4-(benzyloxy)-1-((3-bromo-2-(phenylcarbamoyl)-1H-pyrrol-1-yl)amino)-1-oxobutan-2-yl)carbamate | HCID 131736129 | — |
| Product | (S)-tert-Butyl (3-(benzyloxy)-1-(5-bromo-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamate | HCID 131736130 | 90.3% |
Reaction Steps
(S)-tert-Butyl (4-(benzyloxy)-1-((3-bromo-2-(phenylcarbamoyl)-1H-pyrrol-1-yl)amino)-1-oxobutan-2-yl)carbamate (0.7 g, 1.22 mmol) was treated with triphenylphosphine (0.45 g, 1.72 mmol), bromine (88 μl, 1.72 mmol), triethylamine (683 μl, 4.90 mmol) and sodium methanethiolate (0.17 g, 2.45 mmol) according to the method of Preparation 23. The residue was purified using Isolera® Purification System (0% to 20%, hexane-ethyl acetate) to give 0.61 g (90% yield) of the title compound. Purity 100%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09388189B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-89d2484efba54e83846ec588261ac2a5 |
| Source note | uspto-grants-2016_07 |