Tetrahydrofuran → HCID 58609916, Verbindung

Temperatur

-78 °C

A solution of n-butyl lithium (2.5 M, 250 mL, 0.62 mol) was added to a solution of N-Boc-2-aminothiazole (56 g, 0.28 mol) in anhydrous tetrahydrofuran (500 mL) was added at −78° C. After the addition was completed, the mixture was allowed to stir at −78° C. for one hour. A solution of (2-methoxy-phenyl)-acetaldehyde (36 g, 0.24 mol) in tetrahydrofuran (100 mL) was slowly added to the reaction mixture while maintaining a temperature of −78° C. The mixture was allowed to warm to room temperature and stirred for 15 hours. The reaction was quenched with a saturated aqueous solution of ammonium chloride (1000 mL) and extracted three times with ethyl acetate (400 mL). The combined organic layers were washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate, and evaporated to dryness. The crude product was purified by column chromatography to give the pure product (28 g, 0.080 mol, 28%).

1. additionwas added at −78° C
2. additionAfter the addition
3. temperaturewhile maintaining a temperature of −78° C
4. temperatureto warm to room temperature
5. stirringstirred for 15 hours
6. customThe reaction was quenched with a saturated aqueous solution of ammonium chloride (1000 mL)
7. extractionextracted three times with ethyl acetate (400 mL)
8. washThe combined organic layers were washed with a saturated aqueous solution of sodium chloride
9. dry with materialdried over sodium sulfate
10. customevaporated to dryness
11. customThe crude product was purified by column chromatography

ORD-Eintrag

ord-6c33cdf1efe14b06bbd2feaa337fc178

Quelldatensatz

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08759335B2