HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-{[(4-{[(phenylmethyl)oxy]carbonyl}phenyl)amino]carbonyl}-1-pyrazolidinecarboxylate → 4-({[(3S)-2-((2R)-3-Cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-3-pyrazolidinyl]carbonyl}amino)benzoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-{[(4-{[(phenylmethyl)oxy]carbonyl}phenyl)amino]carbonyl}-1-pyrazolidinecarboxylate | HCID 86706391 | — |
| Catalyst | Palladium hydroxide | HCID 9942167 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 4-({[(3S)-2-((2R)-3-Cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-3-pyrazolidinyl]carbonyl}amino)benzoic acid | HCID 86706392 | 52.3% |
Reaction Steps
To a solution of phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-{[(4-{[(phenylmethyl)oxy]carbonyl}phenyl)amino]carbonyl}-1-pyrazolidinecarboxylate (330 mg, 0.442 mmol) in methanol (20 mL) was added Pd(OH)2/C (330 mg). The mixture was stirred at rt under H2 atmosphere for 2 h. The catalyst was filtered off, the filtrate was concentrated under vacuum, and the residue was purified by preparative HPLC to provide the title compound (100 mg). LCMS: (M+H)+: 482.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08901119B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-824adcd2acfd4f1296a9ef288be1baa1 |
| Source note | uspto-grants-2014_12 |