HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-{[(2S)-1'-{2-[(5R)-3-[3,5-Bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}-N-methyl-N-(3-{methyl[(4-nitrophenyl)acetyl]amino}propyl)acetamide → 2-(4-Aminophenyl)-N-{3-[({[(2S)-1'-{2-[(5R)-3-[3,5-bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)(methyl)amino]propyl}-N-methylacetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-{[(2S)-1'-{2-[(5R)-3-[3,5-Bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}-N-methyl-N-(3-{methyl[(4-nitrophenyl)acetyl]amino}propyl)acetamide | HCID 86663451 | — |
| Catalyst | HCID 178418390 | HCID 178418390 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | 2-(4-Aminophenyl)-N-{3-[({[(2S)-1'-{2-[(5R)-3-[3,5-bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)(methyl)amino]propyl}-N-methylacetamide | HCID 86663452 | 98% |
Reaction Steps
The compound (212 mg, 0.225 mmol) obtained in Example 57a was dissolved in ethanol (10 mL), 10% palladium-carbon (42 mg, 20% by weight) was added, and the mixture was stirred at room temperature under a hydrogen atmosphere for 5 hours. The reaction mixture was filtered through celite, and the solvent was evaporated under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:methanol, 10:1, v/v) to give the title compound (194 mg; yield, 98%) as a yellow oily substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08476253B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-87669a72f7c74c21b3c761c37ffdce99 |
| Source note | uspto-grants-2013_07 |