HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium hydroxy sulfite → Ethyl 3-{[(4-{[cyclohexyl(2-methyl-5-{4-[3-(methylsulfinyl)propoxy]phenyl}furan-3-yl)methyl]amino}phenyl)carbonyl](methyl)amino}propanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium hydroxy sulfite | HCID 23707502 | — |
| Reactant | Ethyl 3-{[(4-{[cyclohexyl(2-methyl-5-{4-[3-(methylsulfanyl)propoxy]phenyl}furan-3-yl)methyl]amino}phenyl)carbonyl](methyl)amino}propanoate | HCID 68514082 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | Ethyl 3-{[(4-{[cyclohexyl(2-methyl-5-{4-[3-(methylsulfinyl)propoxy]phenyl}furan-3-yl)methyl]amino}phenyl)carbonyl](methyl)amino}propanoate | HCID 68509957 | 91% |
Reaction Steps
Ethyl 3-{[(4-{[cyclohexyl(2-methyl-5-{4-[3-(methylsulfanyl)propoxy]phenyl}furan-3-yl)methyl]amino}phenyl)carbonyl](methyl)amino}propanoate (0.37 g) synthesized in Example 259 (1) was dissolved in methanol (9 mL) and water (1 mL), OXONE (221 mg) was added, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (25% ethyl acetate/hexane to 100% ethyl acetate/hexane) to give the title compound (283 mg, 91%) as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08309580B2 |
| Source dataset | uspto-grants-2012_11 |
| ORD ID | ord-a3ff01db3fe34cc1be1962a1b7d5c9dc |
| Source note | uspto-grants-2012_11 |