HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → tert-Butyl {(2S)-1-[(4-chloro-5-nitropyridin-2-yl)oxy]propan-2-yl}carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 1,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate | HCID 7023103 | — |
| Reactant | DIAD toluene | HCID 66880968 | — |
| Reactant | HCID 178526833 | HCID 178526833 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | tert-Butyl {(2S)-1-[(4-chloro-5-nitropyridin-2-yl)oxy]propan-2-yl}carbamate | HCID 86731217 | 45.2% |
Reaction Steps
To a solution of 4-chloro-5-nitropyridin-2-ol (1.00 g), tert-butyl ((2S)-1-hydroxypropan-2-yl)carbamate (1.51 g) and triphenylphosphine (2.25 g) in THF (10 mL) was added dropwise diisopropyl azodicarboxylate toluene solution (1.9 M, 4.52 mL), and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (860 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09133129B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-e74d8aefbfc34a3b96417dba1ee9428c |
| Source note | uspto-grants-2015_09 |