HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 3-Fluorophenylacetic acid, 1,1-dimethyl-2-(4-(methylsulfonyl)phenyl)-2-oxo-ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate | HCID 17220 | — |
| Reactant | 3-Fluorophenylacetic acid | HCID 67617 | — |
| Reactant | 2-Hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one | HCID 15428514 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-Fluorophenylacetic acid, 1,1-dimethyl-2-(4-(methylsulfonyl)phenyl)-2-oxo-ethyl ester | HCID 57265235 | 85.2% |
Reaction Steps
A mixture of 2-hydroxy-4'-(methylsulfonyl)isobutyrophenone (100 g), 3-fluorophenylacetic acid (83 g), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (225 g) and DMAP (25 g) in CH2Cl2 (2 L) was mechanically stirred for 17 h at r.t. A solution of 1M HCl (1 L) was then added and the organic phase was separated, washed with a saturated solution of Na2 CO3 (0.4 L) and dried over MgSO4. After concentration, the residue was purified by silica gel chromatography, eluting with 30% EtOAc/hexanes to give the title compound as a white solid (133 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05698584 |
| Source dataset | uspto-grants-1997_12 |
| ORD ID | ord-c21de5437e2d4be19e2dd877d1c58b38 |
| Source note | uspto-grants-1997_12 |