反应详情

A solution of 3-[(1-methylethyl)oxy]-N-(3-methyl-1,2,4-thiadiazol-5-yl)-5-[(phenylmethyl)oxy]benzamide (33 g, 86 mmol), trifluoroacetic acid (160 mL) and thioanisole (50.5 mL) was stirred at ambient temperature for 48 hours. The TFA was removed in vacuo and the residue poured into saturated sodium bicarbonate solution (300 mL) and extracted into ethyl acetate (twice). The combined organic extracts were washed with brine, dried (MgSO4), filtered and the solvent removed in vacuo. The residue was triturated with DCM and washed with 5% ethyl acetate in isohexane to give the desired compound (12.8 g). 1H NMR δ (d6-DMSO): 1.31 (d, 6H), 2.51 (s, 3H), 4.67 (sept, 1H), 6.58 (s, 1H), 7.08 (s, 1H), 7.24 (s, 1H), 9.88 (s, 1H), 13.25 (brs, 1H). m/z 294 (M+H)+

1. customThe TFA was removed in vacuo
2. additionthe residue poured into saturated sodium bicarbonate solution (300 mL)
3. extractionextracted into ethyl acetate (twice)
4. washThe combined organic extracts were washed with brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. customthe solvent removed in vacuo
8. customThe residue was triturated with DCM
9. washwashed with 5% ethyl acetate in isohexane