HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Sodium Bicarbonate → Racemic Benzyl 2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Sodium Bicarbonate | HCID 516892 | — |
| Edukt | 1-Chloro-N,N-2-trimethylpropenylamine | HCID 640792 | — |
| Edukt | Benzyl 3-(benzoylcarbamothioylamino)-4-(hydroxymethyl)-3-phenyl-pyrrolidine-1-carboxylate | HCID 86697917 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | Racemic Benzyl 2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate | HCID 89832302 | 63,2% |
Reaktionsschritte
1-Chloro-N,N,2-trimethylpropenylamine (17.9 mL, 135 mmol) is added to a 0° C. solution of racemic benzyl 3-(benzoylcarbamothioylamino)-4-(hydroxymethyl)-3-phenyl-pyrrolidine-1-carboxylate (51 g, 104 mmol) in dichloromethane (459 mL) and stirred at room temperature for 2 hours. A saturated solution of sodium hydrogen carbonate (300 mL) is added and the layers are separated. The organic layer is dried over magnesium sulfate, the solution concentrated. The crude product is purified over silica gel eluting with dichloromethane to 5% ethyl acetate/dichloromethane to give the title compound (31 g, 63%). ES/MS (m/e): 372 (M+H).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08629270B2 |
| Quelldatensatz | uspto-grants-2014_01 |
| ORD ID | ord-1e2ac775b6364304917e15226371e4db |
| Quellennotiz | uspto-grants-2014_01 |