반응 #9716

반응 방정식

NH4Cl

trans-2-(trimethylsilyl)ethyl-2-({4′-[(5-methyl-1,3-benzoxazol-2-yl)-amino]biphenyl-4-yl}carbonyl)cyclohexanecarboxylate

tetrabutylammonium fluoride

→

trans-2-({4′-[(5-methyl-1,3-benzoxazol-2-yl)amino]biphenyl-4-yl}carbonyl)cyclohexanecarboxylic acid

수율 84.0%

용매

EtOAc

water

THF

반응 조건

후처리

1. 1
   기타The organic layer was separated
2. 2
   추출the aqueous layer was extracted with EtOAc
3. 3
   세척The combined organic phases were washed with water and brine
4. 4
   건조dried over Na2SO4
5. 5
   여과filtered
6. 6
   기타evaporated under reduced pressure
7. 7
   workup.ADDITIONThe residue was treated with MeOH
8. 8
   여과the precipitate was collected by filtration
9. 9
   기타dried in a vacuum oven

실험 절차

To a solution of trans-2-(trimethylsilyl)ethyl-2-({4′-[(5-methyl-1,3-benzoxazol-2-yl)-amino]biphenyl-4-yl}carbonyl)cyclohexanecarboxylate (64 mg, 0.12mmol) in THF (2 mL) was added tetrabutylammonium fluoride (1.0 M in THF, 0.70 mL), and then the reaction mixture was stirred at rt for 16 h. Saturated aqueous NH4Cl was added, and the reaction mixture was diluted with EtOAc and water. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic phases were washed with water and brine, dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was treated with MeOH, and the precipitate was collected by filtration and dried in a vacuum oven to give trans-2-({4′-[(5-methyl-1,3-benzoxazol-2-yl)amino]biphenyl-4-yl}carbonyl)cyclohexanecarboxylic acid (44.3 mg, 84%). LC-MS m/z 455.3 (MH+), ret. time 3.57 min. 1H NMR (400 MHz, DMSO-d6) δ 1.21 (m, 1H), 1.37 (m, 2H), 1.63 (m, 1H), 1.85 (m, 3H), 2.05 (m, 1H), 2.38 (s, 3H), 2.69 (m, 1H), 3.95 (m, 1H), 7.03 (d, 1H), 7.33 (d, 2H), 7.76 (m, 4H), 7.85 (d, 2H), 7.93 (d, 2H), 10.73 (s, 1H).

출처