反应详情

A solution of (±)-3-{4-[2-cyclohexyl-1-(4′-trifluoromethyl-biphenyl-4-yl)-ethoxy]-benzoylamino}-propionic acid tert-butyl ester (0.0910 g, 0.153 mmol) in dimethylformamide (1.0 mL) at 0° C. was treated with NaH (1 small spatula tip). After 25 min., MeI (0.0240 mL, 0.385 mmol) is added and the reaction is stirred for 1 h. The reaction mixture is quenched with saturated NH4Cl (aq) (2 μL) and extracted with EtOAc (3×10 mL). Combined extracts are washed with brine (1×), dried over MgSO4, filtered, and conc. The residue is loaded onto silica gel and eluted with hexanes using a gradient of 10% EtOAc to 60% EtOAc giving (±)-3-({4-[2-cyclohexyl-1-(4′-trifluoromethyl-biphenyl-4-yl)-ethoxy]-benzoyl}-methyl-amino)-propionic acid tert-butyl ester (7.4 mg, 8%) as a clear syrup. MS (ES): 554.0 [M+H-(t-Bu)]+.

1. customThe reaction mixture is quenched with saturated NH4Cl (aq) (2 μL)
2. extractionextracted with EtOAc (3×10 mL)
3. washCombined extracts are washed with brine (1×)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. washeluted with hexanes using a gradient of 10% EtOAc to 60% EtOAc