HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl N-(triethylammoniosulfonyl)carbamate → (S)-t-Butyl 2-(5-(((tert-butyldiphenylsilyl)oxy)methyl)-1,3,4-oxadiazol-2-yl)pyrrolidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl N-(triethylammoniosulfonyl)carbamate | HCID 2724994 | — |
| Reactant | (S)-t-Butyl 2-(2-(2-((tert-butyldiphenylsilyl)oxy)acetyl)hydrazinecarbonyl)pyrrolidine-1-carboxylate | HCID 86706754 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | (S)-t-Butyl 2-(5-(((tert-butyldiphenylsilyl)oxy)methyl)-1,3,4-oxadiazol-2-yl)pyrrolidine-1-carboxylate | HCID 86706755 | 73.2% |
Reaction Steps
To a toluene (112 mL) solution of the compound (5.87 g) obtained in Example 9-(1), Burgess reagent (5.322 g) was added and the mixture was heated under reflux for 2.5 hours. The reaction mixture was concentrated to give a crude product, which was further purified by silica gel chromatography (AcOEt/hexane) to give the titled compound (4.151 g, colorless amorphous.)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09181229B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-49a047edf3524832b3c418e309dca408 |
| Source note | uspto-grants-2015_11 |