HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Nitro-N-[(prop-2-en-1-yl)oxy]benzene-1-sulfonamide → (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-3,4-dimethyl-5,6-dihydropyridine-1 (2H)-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Nitro-N-[(prop-2-en-1-yl)oxy]benzene-1-sulfonamide | HCID 15497911 | — |
| Reactant | (2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-3,4-dimethyl-5,6-dihydropyridine-1(2H)-carboxylate | HCID 89852353 | — |
| Reactant | (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-4-methyl-5,6-dihydropyridine-1(2H)-carboxylate | HCID 89852484 | — |
| Product | (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-3,4-dimethyl-5,6-dihydropyridine-1 (2H)-carboxylate | HCID 89852224 | 110.5% |
Reaction Steps
The title compound was prepared from (2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-3,4-dimethyl-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 191, 1.73 g, 4.66 mmol) and N-(allyloxy)-2-nitrobenzenesulfonamide (Intermediate 9, 1.26 g, 4.89 mmol) following the procedure described for Intermediate 10. Silica gel chromatography (0%-20% ethyl acetate/hexanes) afforded the desired product as an off-white solid (3.15 g, 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09309245B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-e056780fa6114717afb4ae5fc5dc9b86 |
| Source note | uspto-grants-2016_04 |