HuagongsheHuagongshe Chemistry Print Report · For research reference only
Aldoxime → 3-[2-(3-Methyl-isoxazol-5-yl)-pyridin-4-yl]-3-oxo-propionic acid tert.-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Aldoxime | HCID 7863 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Chlorosuccinimide | HCID 31398 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | Methyl 2-iodoisonicotinate | HCID 196869 | — |
| Reactant | 2-(3-Methyl-isoxazol-5-yl)-isonicotinic acid methyl ester | HCID 69687972 | — |
| Reactant | Lithium Tert-butyl Acetate | HCID 86586795 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 3-[2-(3-Methyl-isoxazol-5-yl)-pyridin-4-yl]-3-oxo-propionic acid tert.-butyl ester | HCID 69688172 | — |
Reaction Steps
The title compound was prepared from 2-(3-methyl-isoxazol-5-yl)-isonicotinic acid methyl ester [prepared by i.) reaction of 2-iodo-isonicotinic acid methyl ester [CAS-No. 134579-47-8] with trimethylsilylacetylene according to general procedure H; ii.) desilylation by reaction with cat. K2CO3 in MeOH at 0° C. for 4 h; iii.) cycloadditon with a mixture of NCS, acetaldoxime, Et3N and cat. amount of pyridine in CHCl3 at 50° C. according to Tetrahedron 1984, 40, 2985-2988] by treatment with lithium tert.-butyl acetate according to general procedure K (method b). Obtained as a brown solid (5.17 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06544985B2 |
| Source dataset | uspto-grants-2003_04 |
| ORD ID | ord-ecde33b9de96434a94df97d29cff0ae0 |
| Source note | uspto-grants-2003_04 |