反应详情

温度

-78 °C

To a solution of lithium diisopropylamide (prepared in situ) (4.24 g, 39.6 mmol) in dry THF (40 mL) was added the solution of {2-[tert-butoxycarbonyl-(4-methoxy-benzyl)-amino]-thiazol-4-yl}-acetic acid ethyl ester (8.0 g, 19.68 mmol) in 20 mL of dry THF in a dropwise fashion at −78° C. The reaction mixture was continued to stir at −78° C. for 1 hour followed by the addition of methyl iodide (4.19 g, 29.52 mmol) at the same temperature. The reaction mixture was kept on stirring and slowly allowed to come to room temperature. The reaction mixture was quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layer was washed with brine and dried over anhydrous sodium sulphate and the solvent was removed in vacuo to get the sticky compound (8.2 g). The compound was used for the next reaction without any purification.

1. stirringon stirring
2. customto come to room temperature
3. customThe reaction mixture was quenched with saturated ammonium chloride solution
4. additiondiluted with ethyl acetate
5. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
6. washThe combined organic layer was washed with brine
7. dry with materialdried over anhydrous sodium sulphate
8. customthe solvent was removed in vacuo