Triethylamine → [3,3''-Dichloro-5'-(8-indol-1-yl-octylcarbamoyl)-[1,1';3',1'']terphenyl-2'-yloxy]-ethanol

To a flame dried round bottom flask with 8-indol-1-yloctylamine (0.227 g, 0.930 mmol, preparation similar to step 1 of Example 54) in CH2Cl2 (10 mL) at room temperature was added 3,5-bis-(m-chlorophenyl)-4-(2-hydroxyethoxy)-benzoic acid (0.250 g, 0.620 mmol, prepared in step 2 of Example 55) followed by Et3N (0.259 mL, 1.86 mmol), HOBt (0.092 g, 0.682 mmol), and finally DCC (0.153 g, 0.744 mmol). After 3 days at this temperature, it was concentrated and then diluted with EtOAc (200 mL). The white solid (DCU) that formed was filtered off and washed with excess EtOAc. The organic layer was washed with 1 N HCl (20 mL), sat. aq. NaHCO3 (20 mL), and brine (20 mL) and then dried (MgSO4). After concentration, the residue was purified by the Biotage Flash 40 apparatus (30 to 50% EtOAc/petroleum ether) to afford the product (0.341 g, 87%) as a solid; 1H NMR (CDCl3) δ 1.21–1.38 (m, 8H), 1.46–1.63 (m, 3H), 1.75–1.89 (m, 2H), 3.27–3.49 (m, 6H), 4.11 (t, J=8.1 Hz, 2H), 6.01–6.13 (m, 1H), 6.47 (d, J=2.2 Hz, 1H), 7.05–7.13 (m, 2H), 7.19 (t, J=8.8 Hz, 1H), 7.39–7.46 (m, 5H), 7.48–7.55 (m, 2H), 7.58–7.66 (m, 3H), 7.74 (s, 2H); mass spectrum [(+) ESI], m/z 629 (M)+.

1. concentrationAfter 3 days at this temperature, it was concentrated
2. additiondiluted with EtOAc (200 mL)
3. customThe white solid (DCU) that formed
4. filtrationwas filtered off
5. washwashed with excess EtOAc
6. washThe organic layer was washed with 1 N HCl (20 mL), sat. aq. NaHCO3 (20 mL), and brine (20 mL)
7. dry with materialdried (MgSO4)
8. concentrationAfter concentration
9. customthe residue was purified by the Biotage Flash 40 apparatus (30 to 50% EtOAc/petroleum ether)

ORD 기록

ord-5487ba1fa8f94024818b6b5fdc507e63

출처 데이터셋

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07008636B2