Sodium Iodide → 2-Methyl-2-propanyl {(1S)-2-{4-[(2-methyl-1,3-thiazol-4-yl)methoxy]phenyl}-1-[(2S)-2-oxiranyl]ethyl}carbamate

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Reaction Conditions

Reaction Steps

0.6 g (3.26 mmol) 4-Chloromethyl-2-methyl-thiazole hydrochloride was added to a stirred solution of 0.76 g (2.71 mmol) tert-butyl (1S)-2-(4-hydroxyphenyl)-1-[(2S)-oxiranyl]ethylcarbamate in 15 ml N,N-dimethylformamide. 3.25 g (10 mmol) cesium carbonate and 550 mg (3.66 mmol) sodium iodide was added, and the mixture was stirred at 20° C. for 24 hours. 200 ml ethyl acetate was added, and the mixture was filtered. The filtrate was extracted with water (5×50 ml), and the organic phase was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified on silicagel column using hexane-ethyl acetate (1:1) as solvent to yield 820 mg (Y=78%) title compound. 1H-NMR (CDCl3): δ 1.36 (9H,s), 2.71 (3H,s), 2.75-2.95 (4H,m), 3.61 (1H,s(br)), 4.39 (1H,s(br)), 5.11 (2H,s), 6.91 (2H,d), 7.11 (2H,d), 7.12 (1H,s).

Provenance & Evidence