HuagongsheHuagongshe Chemistry Print Report · For research reference only
Aniline → (S)-tert-Butyl (4-(benzyloxy)-1-((3-bromo-2-(phenylcarbamoyl)-1H-pyrrol-1-yl)amino)-1-oxobutan-2-yl)carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Aniline | HCID 6115 | — |
| Reactant | Trimethylaluminum | HCID 16682925 | — |
| Reactant | (S)-Methyl 1-(4-(benzyloxy)-2-(tert-butoxycarbonylamino)butanamido)-3-bromo-1H-pyrrole-2-carboxylate | HCID 86722060 | — |
| Product | (S)-tert-Butyl (4-(benzyloxy)-1-((3-bromo-2-(phenylcarbamoyl)-1H-pyrrol-1-yl)amino)-1-oxobutan-2-yl)carbamate | HCID 131736129 | 63.4% |
Reaction Steps
(S)-Methyl 1-(4-(benzyloxy)-2-((tert-butoxycarbonyl)amino)butanamido)-3-bromo-1H-pyrrole-2-carboxylate (1 g, 1.96 mmol) was treated with aniline (893 μl, 9.8 mmol) and trimethyl aluminium (2 M in toluene, 4.9 mL, 9.8 mmol) according to the method of Preparation 10a. The residue was purified using SP1® Purification System (0% to 30%, hexane-ethyl acetate) a to obtain 0.71 g (63% 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-998b266345f3427eb878c65965f991ec |
| Source note | uspto-grants-2016_07 |