反应详情

A solution of 0.137 g (0.375 mmol) of trans-4-[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexanecarboxylic acid in 2 mL of CH2Cl2 was treated at RT with 1 drop of DMF, followed by 0.035 mL (0.412 mmol, 1.1 eq) of oxalyl chloride within 5 min, and stirring was continued for 90 min. The solution was evaporated, redissolved in 2 mL of CH2Cl2 and treated with 0.058 mL (0.450 mmol, 1.2 eq) of N,N,N′-trimethylethylenediamine at 0° C. The reaction was kept at RT for 2 h, then partitioned between Et2O (×3)/aqueous saturated NaHCO3. The organic phases were washed once with 10% aqueous NaCl, dried over Na2SO4 and evaporated. Purification by flash-chromatography on 8 g of silica gel (CH2Cl2:MeOH 99:1 to 9:1) gave 0.088 g (53%) of pure trans-4-[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexanecarboxylic acid (2-dimethylamino-ethyl)-methyl-amide, MS: 450 (MH+), MP: 83° C.

1. customThe solution was evaporated
2. dissolutionredissolved in 2 mL of CH2Cl2
3. waitThe reaction was kept at RT for 2 h
4. custompartitioned between Et2O (×3)/aqueous saturated NaHCO3
5. washThe organic phases were washed once with 10% aqueous NaCl
6. dry with materialdried over Na2SO4
7. customevaporated
8. customPurification by flash-chromatography on 8 g of silica gel (CH2Cl2:MeOH 99:1 to 9:1)