反应详情

A solution of tert-butyl N-[4-(methanesulfonyloxy)cyclohexyl]carbamate (2.24 g, 7.64 mmol, 1.00 equiv), methyl 4-[5-methyl-4-(sulfanylmethyl)-1,3-oxazol-2-yl]benzoate (3.0 g, 11.39 mmol, 1.20 equiv) and cesium carbonate (5.55 g, 16.98 mmol, 2.00 equiv) in N,N-dimethylformamide (30 mL) was stirred at 50° C. under nitrogen atmosphere for 3 h. Water (100 mL) was added to quench the reaction. The resulting solution was extracted with 3×80 mL of ethyl acetate. The combined organic layers was washed with 2×200 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1:15-2:1) to give 960 mg (27%) of methyl 4-(4-[[(4-[[(tert-butoxy)carbonyl]amino]cyclohexyl)sulfanyl]methyl]-5-methyl-1,3-oxazol-2-yl)benzoate as a yellow solid. LC-MS: (ES, m/z): 461 [M+H]+, 405, 271, 230, 102.

1. customto quench
2. customthe reaction
3. extractionThe resulting solution was extracted with 3×80 mL of ethyl acetate
4. washThe combined organic layers was washed with 2×200 mL of brine
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under vacuum
7. customThe residue was purified on a silica gel column
8. washeluted with ethyl acetate/petroleum ether (1:15-2:1)