Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | HCID 22013856 | HCID 22013856 | — |
| Solvent | Tetrahydrofurane dichloromethane | HCID 21919333 | — |
| Product | HCID 22013852 | HCID 22013852 | 17% |
Reaction Steps
To a solution of 2-hydroxy-3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propionamide (550 mg, 1.50 mmol) obtained in Example 36 in dichloromethane-tetrahydrofuran (1:1, 50 ml) was added equivalent of methyl chlorofornate and triethylamine under ice-cooling until the reaction completed. The mixture was stirred for 1 hr, and the reaction mixture was diluted with ethyl acetate (100 ml) and washed successively with saturated brine, 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated brine. The mixture was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent; dichloromethane:methanol=98:2) to give the title compound (110 mg, yield 17%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06204277B1 |
|---|
| Source dataset | uspto-grants-2001_03 |
|---|
| ORD ID | ord-eb4dd5e7c6334ffb914118d75bd75249 |
|---|
| Source note | uspto-grants-2001_03 |
|---|