HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → (5R)-3-[3-Fluoro-4-(4-methyl-1H-1,2,3-triazol-1-yl)phenyl]-5-[(5-methyl-2H-tetrazol-2-yl)methyl]oxazolidin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | 5-methyl-2H-tetrazole | HCID 138107 | — |
| Reactant | (5R)-3-[3-Fluoro-4-(4-methyl-1,2,3-triazol-1-yl)phenyl]-5-(hydroxymethyl)oxazolidin-2-one | HCID 57526994 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (5R)-3-[3-Fluoro-4-(4-methyl-1H-1,2,3-triazol-1-yl)phenyl]-5-[(5-methyl-2H-tetrazol-2-yl)methyl]oxazolidin-2-one | HCID 10089750 | 44.1% |
Reaction Steps
This compound was prepared from (5R)-3-[3-Fluoro-4-(4-methyl-1H-1,2,3-triazol-1-yl)phenyl]-5-(hydroxymethyl)oxazolidin-2-one (Intermediate 19) (1.054 g, 3.61 mmol) and 5-methyl-2H-tetrazole (0.608 g, 7.23 mmol), as described for Example 29. Chromatography on silica gel with 5% methanol in dichloromethane gave the crude product (0.72 g) which was purified further by trituration with dichloromethane and diethyl ether to afford the title product (0.571 g). The regioisomeric product (5R)-3-[3-fluoro-4-(4-methyl-1H-1,2,3-triazol-1-yl)phenyl]-5-[(5-methyl-1H-tetrazol-1-yl)methyl]-1,3-oxazolidin-2-one was also isolated (0.228 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07473699B2 |
| Source dataset | uspto-grants-2009_01 |
| ORD ID | ord-7780d2add0bb48e793e385b93583c101 |
| Source note | uspto-grants-2009_01 |