HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (S)-Methyl 1-(4-(benzyloxy)-2-(tert-butoxycarbonylamino)butanamido)-3-bromo-1H-pyrrole-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Propylphosphonic anhydride | HCID 111923 | — |
| Reactant | O-Benzyl-N-(tert-butoxycarbonyl)-L-homoserine | HCID 15058464 | — |
| Reactant | methyl 1-amino-3-bromo-1H-pyrrole-2-carboxylate | HCID 70979762 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (S)-Methyl 1-(4-(benzyloxy)-2-(tert-butoxycarbonylamino)butanamido)-3-bromo-1H-pyrrole-2-carboxylate | HCID 86722060 | 102.7% |
Reaction Steps
Methyl 1-amino-3-bromo-1H-pyrrole-2-carboxylate (2.83 g, 12.92 mmol) was treated with (S)-4-(benzyloxy)-2-((tert-butoxycarbonyl)amino)butanoic acid (4 g, 12.93 mmol), N,N-diisopropylethylamine (7.4 mL, 42.6 mmol) and T3P® (50% in ethyl acetate, 10.8 mL, 18.14 mmol) according to the method of Preparation 5a to give 6.77 g (84% yield) of the desired compound. Purity 81%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09388189B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-edf7e7e065364c0f88431356025119c3 |
| Source note | uspto-grants-2016_07 |