HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (5R)-3-[4-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl]-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (5S)-5-(Aminomethyl)-3-[4-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl]oxazolidin-2-one | HCID 57526982 | — |
| Reactant | 1,1-Dichloroacetone toluenesulfonylhydrazone | HCID 86598067 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (5R)-3-[4-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl]-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one | HCID 10367222 | 46.7% |
Reaction Steps
(5S)-5-(Aminomethyl)-3-[4-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-3,5-diflurophenyl]-1,3-oxazolidin-2-one (Intermediate 54) (3.20 g, 8.01 mmol) was reacted with diisopropylethylamine (5.60 ml, 32.04 mmol) and 1,1-dichloroacetone toluenesulfonylhydrazone (2.8 g, 9.6 mmol) as described for Example 3. Chromatography on silica gel with ethyl acetate gave 1.74 g of the title product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07473699B2 |
| Source dataset | uspto-grants-2009_01 |
| ORD ID | ord-ddd7b6509243494385681f61b4581c82 |
| Source note | uspto-grants-2009_01 |