HuagongsheHuagongshe Chemistry Print Report · For research reference only
Bromopinacolone → (S)-2-{[5-(3,3-Dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-pentanedioic acid 5-tert-butyl ester 1-methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Bromopinacolone | HCID 21642 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | HCID 178501468 | HCID 178501468 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (S)-2-{[5-(3,3-Dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-pentanedioic acid 5-tert-butyl ester 1-methyl ester | HCID 66920060 | — |
Reaction Steps
Crude (S)-2-[(5-Hydroxy-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester (44 g) was dissolved in DMF and treated with 12.2 g potassium tert-butoxide and 14.7 ml 1-bromopinacolone. After 2 h the solvent was removed in vacuo, the residue taken up in DCM and extracted with water. The crude product obtained after evaporation of the solvent was purified by flash column chromatography on silica eluting with heptane/ethyl acetate giving the title compound as colorless oil (45 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08598179B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-a13c9b70cec04809a99fb89fc9ce525c |
| Source note | uspto-grants-2013_12 |