HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → 4-[2-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-oxazol-5-yl]-2-isobutyl-6-methyl-pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Methyl N-(triethylammoniosulfonyl)carbamate | HCID 2724994 | — |
| Reactant | 4-benzyloxy-3-ethyl-N-[2-(2-isobutyl-6-methyl-pyridin-4-yl)-2-oxo-ethyl]-5-methyl-benzamide | HCID 68552785 | — |
| Product | 4-[2-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-oxazol-5-yl]-2-isobutyl-6-methyl-pyridine | HCID 68553908 | — |
Reaction Steps
To a solution 4-benzyloxy-3-ethyl-N-[2-(2-isobutyl-6-methyl-pyridin-4-yl)-2-oxo-ethyl]-5-methyl-benzamide (70 mg, 0.153 mmol) in THF (2 mL), Burgess reagent (95 mg, 0.377 mmol) is added and the mixture is refluxed for 2 h. Another portion of Burgess reagent (50 mg, 0.231 mmol) is added and stirring is continued at rt for 16 h. The solvent is evaporated and the crude product is purified on prep. TLC with heptane:EA 1:2 to give 4-[2-(4-benzyloxy-3-ethyl-5-methyl-phenyl)-oxazol-5-yl]-2-isobutyl-6-methyl-pyridine (24 mg) as a yellow oil; LC-MS: tR=1.33*, [M+1]+=441.04.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08580824B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-50020277fcfa4d1bb679398644e96edc |
| Source note | uspto-grants-2013_11 |