HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Hydrochloric Acid → (3R)-4-Amino-3-(3-{[(3,4-dichlorophenyl)sulfonyl]amino}-4-chlorophenyl)butanoic acid
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Hydrochloric Acid | HCID 313 | — |
| Edukt | Benzenesulfonyl chloride, 3,4-dichloro- | HCID 7383 | — |
| Edukt | Diisopropylethylamine | HCID 81531 | — |
| Edukt | (4R)-4-(3-amino-4-chlorophenyl)pyrrolidin-2-one | HCID 66724932 | — |
| Edukt | (3R)-4-amino-3-(3-bromo-4-chlorophenyl)butanoic acid hydrochloride | HCID 66725034 | — |
| Katalysator | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | (3R)-4-Amino-3-(3-{[(3,4-dichlorophenyl)sulfonyl]amino}-4-chlorophenyl)butanoic acid | HCID 49793116 | — |
Reaktionsschritte
(4R)-4-(3-Amino-4-chlorophenyl)pyrrolidin-2-one (0.105 g, 0.5 mmol) was dissolved in 2 mL of methylene chloride (2 mL). Diisopropylethylamine (0.14 mL, 0.75 mmol) was added followed by 3,4-dichlorobenzenesulfonyl chloride (0.134 g, 0.55 mmol) and a catalytic amount of DMAP (0.05 mmol). The mixture was stirred overnight at room temperature. The mixture was then diluted with methylene chloride (50 mL), washed with water, then brine, and concentrated to give the product, which was treated with HCl as described for the preparation of (3R)-4-amino-3-(3-bromo-4-chlorophenyl)butanoic acid hydrochloride to provide the title compound (21). MS (ESI) m/z 438.89 (M+H)+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08344028B2 |
| Quelldatensatz | uspto-grants-2013_01 |
| ORD ID | ord-b680394f819f43e796659c48df9f4f3a |
| Quellennotiz | uspto-grants-2013_01 |