Potassium Carbonate → Benzyl 2-(3-amino-1,2,4-thiadiazol-5-YL)pyrrolidine-1-carboxylate
Reaktionsgleichung
Br.[CH2:2]([O:9][C:10]([N:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[C:17]1[S:21][N:20]=[C:19]([NH:22]C(=O)C)[N:18]=1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+]>C(O)C.O>[CH2:2]([O:9][C:10]([N:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[C:17]1[S:21][N:20]=[C:19]([NH2:22])[N:18]=1)=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1Komponenten
5
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
2-(3-Acetylamino-[1,2,4]thiadiazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester hydrobromide (14.0 g, 37.8 mmol) was dissolved in ethanol (80 mL). The reaction mixture was cooled to 0° C. and a solution of K2CO3 (15.0 g, 108.7 mmol) in H2O (40 mL) was added. The solution was allowed to return to room temperature while stirring for 30 mins. The solution was concentrated down, redissolved in water (100 mL) and extracted with DCM (3×50 mL). The organic layers were combined and washed with brine (3×50 mL). The organic layer was partitioned from the aqueous layer, dried over MgSO4 and concentrated under vacuo to afford 9.4 g (94%) of 2-(3-amino-[1,2,4]thiadiazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester as a yellow oil.
Aufarbeitung
- customto return to room temperature
- concentrationThe solution was concentrated down
- dissolutionredissolved in water (100 mL)
- extractionextracted with DCM (3×50 mL)
- washwashed with brine (3×50 mL)
- customThe organic layer was partitioned from the aqueous layer
- dry with materialdried over MgSO4
- concentrationconcentrated under vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-52e89bc613294643ba254eabd0ffe2bc
- Quelldatensatz
- uspto-grants-2010_11
- Patentnummer
- US07825256B2
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