HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hexamethyldisilazide → (5R)-3-{3-Fluoro-4-[4-(methylthio)-1H-1,2,3-triazol-1-yl]phenyl}-5-(hydroxymethyl)-oxazolidin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | [3-Fluoro-4-[4-(methylthio)-1H-1,2,3-triazol-1-yl]phenyl] carbamic acid benzyl ester | HCID 57526960 | — |
| Reactant | (5R)-3-[3-Fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]-5-(hydroxymethyl)oxazolidin-2-one | HCID 57526987 | — |
| Product | (5R)-3-{3-Fluoro-4-[4-(methylthio)-1H-1,2,3-triazol-1-yl]phenyl}-5-(hydroxymethyl)-oxazolidin-2-one | HCID 57526965 | — |
Reaction Steps
[3-Fluoro-4-[4-(methylthio)-1H-1,2,3-triazol-1-yl]phenyl] carbamic acid benzyl ester (Intermediate 49) (27.4 g, 76.5 mmol), LiHMDS (1M in THF, 91 ml) and R-(−)-glycidyl butyrate (11.5 g, 79.7 mmol) were reacted following the procedure for Intermediate 25 to give the crude title compound (19.4 g), which was used without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07473699B2 |
| Source dataset | uspto-grants-2009_01 |
| ORD ID | ord-8b4d0cc5daef42b2b77b9f71a236adf0 |
| Source note | uspto-grants-2009_01 |