Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | 1-Methylimidazole | HCID 1390 | — |
| Edukt | Methanesulfonyl chloride | HCID 31297 | — |
| Edukt | (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid | HCID 86706346 | — |
| Edukt | HCID 178507601 | HCID 178507601 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | HCID 178523396 | HCID 178523396 | 51,1% |
Reaktionsschritte
To a solution of (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidine carboxylic acid (176 mg, 0.327 mmol) in DMF (2 ml) was added 1-methylimidazole (52 μl, 0.655 mmol) and cooled to 0° C. Mesyl chloride (27 μL, 0.344 mmol) was added dropwise at 0° C., and the resulting mixture was stirred for 30 min followed by the addition of 2-amino pyridine N-oxide (36 mg, 0.327 mmol). The reaction was warmed to rt. After 2 h, the reaction mixture was concentrated, diluted with methanol, and purified by reverse phase HPLC to afford 105 mg (0.167 mmol, 51%) of the title compound. LC/MS: (M+H)+: 629.8.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patentnummer | US08901119B2 |
|---|
| Quelldatensatz | uspto-grants-2014_12 |
|---|
| ORD ID | ord-dcf1187568b94db88d5615ca40736924 |
|---|
| Quellennotiz | uspto-grants-2014_12 |
|---|