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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 470248Erstellt: 24. Oktober 2026

Sodium Bicarbonate → Racemic Benzyl 2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

https://huagongshe.com/de/reaction/470248

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktSodium BicarbonateHCID 516892—
Edukt1-Chloro-N,N-2-trimethylpropenylamineHCID 640792—
EduktBenzyl 3-(benzoylcarbamothioylamino)-4-(hydroxymethyl)-3-phenyl-pyrrolidine-1-carboxylateHCID 86697917—
LösungsmittelDichloromethaneHCID 6344—
ProduktRacemic Benzyl 2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylateHCID 8983230263,2%

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

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08629270B2
Quelldatensatzuspto-grants-2014_01
ORD IDord-1e2ac775b6364304917e15226371e4db
Quellennotizuspto-grants-2014_01