HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanesulfonyl chloride → 2,2-dichloro-1-((4S,5R)-5-(4-(6-(chloromethyl)pyridin-3-yl)phenyl)-4 (fluoromethyl)-2,2-dimethyloxazolidin-3-yl)ethanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2,2-dichloro-1-((4S,5R)-4-(fluoromethyl)-5-(4-(6-(hydroxymethyl)pyridin-3-yl)phenyl)-2,2-dimethyloxazolidin-3-yl)ethanone | HCID 86695406 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2,2-dichloro-1-((4S,5R)-5-(4-(6-(chloromethyl)pyridin-3-yl)phenyl)-4 (fluoromethyl)-2,2-dimethyloxazolidin-3-yl)ethanone | HCID 86713164 | 97.5% |
Reaction Steps
To a cooled (ice-water) solution of the product of step 1 (800 mg, 1.87 mmol) and DIPEA (0.675 mL, 3.75 mmol) in DCM (10 mL) is slowly added methanesulfonyl chloride (0.150 mL, 1.87 mmol). The reaction mixture is stirred at room temperature for 6 hours. The reaction is diluted with DCM (10 mL), washed with water (2×10 mL) dried over Na2SO4 and concentrated under reduced pressure to give the title compound (813 mg): LCMS m/z (Cl): 445 [M+H].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09206126B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-63de992dc7ad49eea645a79efe833794 |
| Source note | uspto-grants-2015_12 |