2,4-Dimethylaniline → 3(RS)-(tert-butoxyformamido)-5,5,5-trifluoro-2(RS)-hydroxy-2',4' dimethylvaleranilide

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Reaction Steps

A mixture of 287 mg (1 mmol) of 3(RS)-(tert-butoxyformamido)-5,5,5-trifluoro-2(RS)-hydroxyvaleric acid, 363 mg (3 mmol) of 2,4-dimethylaniline, 288 mg (1.5 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 150 mg (1.1 mmol) of 1-hydroxybenzotriazole in 10 ml of dichloromethane was stirred at room temperature for 2 hours. The solution was diluted with diethyl ether, washed with 2M hydrochloric acid and saturated sodium bicarbonate solution and then dried over anhydrous magnesium sulphate, filtered and evaporated to give 363 mg of 3(RS)-(tert-butoxyformamido)-5,5,5-trifluoro-2(RS)-hydroxy-2′,4′ dimethylvaleranilide as a white solid, 1H NMR (250 MHz, CDC3) δ: 1.4 (s,4H), 1.45 (s,5H), 2.1 (s,1.5H), 2.15 (s, 1.5H), 2.3 (s,3H), 2.2-2.6 (m,1H), 2.7-3(m,1H), 4.2-4.6 (m,2H), 5.3 (d,0.5H), 5.6 (d,0.5H), 5.9 (d,0.5H), 6.2 (d,0.5H), 7.0 (m,2H), 7.6 (d,0.5H), 7.7 (d,0.5H), 8.6 (s,1H).

Provenance & Evidence