Benzylamine → HCID 68702539, Verbindung

To a solution of 2-(tert-butoxycarbonyl(methyl)amino)-4-methylthiazole-5-carboxylic acid (0.070 g, 0.26 mmol) in dichloromethane (2 mL) at 0° C. was added N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.15 g, 0.39 mmol), followed by the addition of benzylamine (29.5 μL, 0.27 mmol), 4-dimethylaminopyridine (catalytical amount), and triethylamine (72 μL, 0.52 mmol). The reaction mixture was allowed to warm to ambient temperature over 3 h, followed by the addition of saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography eluting with ethyl acetate/hexanes (5/95 to 100/0) to afford tert-butyl 5-(benzylcarbamoyl)-4-methylthiazol-2-yl(methyl)carbamate (0.030 g, 0.083 mmol).

1. extractionThe mixture was extracted with ethyl acetate
2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customThe crude product was purified by flash column chromatography
6. washeluting with ethyl acetate/hexanes (5/95 to 100/0)

ORD-Eintrag

ord-d7dbcd892c6749cc8cb9259ca3bae5dd

Quelldatensatz

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08541457B2