HuagongsheHuagongshe Chemistry Print Report · For research reference only
(R)-propionic acid (acetyl-{3-[4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamoyloxy)-methyl ester → (S)-2,2-dimethyl-propionic acid 3-[4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethylcarbamoyloxymethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (R)-propionic acid (acetyl-{3-[4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamoyloxy)-methyl ester | HCID 11386734 | — |
| Reactant | 2,2-Dimethyl-propanoyloxymethyl carbonochloridate | HCID 14800980 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (S)-2,2-dimethyl-propionic acid 3-[4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethylcarbamoyloxymethyl ester | HCID 58958556 | 85% |
Reaction Steps
Following general procedure C, (S)-5-aminomethyl-3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-oxazolidin-2-one (2) (472.0 mg, 1.38 mmol) in dichloromethane (13 mL) and 2,2-dimethyl-propanoyloxymethyl carbonochloridate (7f) gave the titled product in 85% yield (585.6 mg, 1.17 mmol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07265140B2 |
| Source dataset | uspto-grants-2007_09 |
| ORD ID | ord-e34b3deb3c6649aa990e5c5c8aab0e79 |
| Source note | uspto-grants-2007_09 |