Download (6Mb) - Etheses - Saurashtra University

Chapter-5
Synthesis of highly substituted pyrroles
tert-butyl 2-((4R,6R)-6-(2-(3-((3-chloro-4-fluorophenyl)carbamoyl)-5-(4-fluorophenyl)-2-isopropyl-4-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)
acetate AS-18. White solid, mp 144-146 ° C; R f 0.46 (9:1 Chloroform: Methanol); IR
(KBr): 3399, 3053, 2975, 2982, 2875, 1736, 1684, 1564, 1573, 1475, 1283, 1062,
1041, 833, 781, 752, 703 cm -1 ; MS (m/z): 706 [M + ]; Anal. Calcd for C 40 H 45 ClF 2 N 2 O 5 :
C, 67.93; H, 6.41; N, 3.96; Found: C, 67.94; H, 6.42; N, 3.97.
tert-butyl 2-((4R,6R)-6-(2-(3-((3,4-dichlorophenyl)carbamoyl)-5-(4-fluorophenyl)
-2-isopropyl-4-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate
AS-19. White solid, mp 136-138 ° C; R f 0.38 (9:1 Chloroform: Methanol); IR (KBr):
3425, 2964, 2974, 2863, 1756, 1672, 1575, 1549, 1457, 1288, 1068, 1053, 836, 764,
772, 719 cm -1 ; MS (m/z): 722 [M + ]; Anal. Calcd for C 40 H 45 Cl 2 FN 2 O 5 : C, 66.39; H,
6.27; N, 3.87; Found: C, 66.40; H, 6.30; N, 3.88.
tert-butyl 2-((4R,6R)-6-(2-(3-((2,3-dimethylphenyl)carbamoyl)-5-(4-fluorophenyl)
-2-isopropyl-4-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate
AS-20. White solid, mp 180-182 ° C; R f 0.41 (9:1 Chloroform: Methanol); IR (KBr):
3417, 3048, 2957, 2985, 2875, 1748, 1663, 1557, 1579, 1457, 1285, 1052, 1038, 857,
757, 763, 709 cm -1 ; MS (m/z): 682 [M + ]; Anal. Calcd for C 42 H 51 FN 2 O 5 : C, 73.87; H,
7.53; N, 4.10; Found: C, 73.84; H, 7.54; N, 4.12.
tert-butyl 2-((4R,6R)-6-(2-(2-cyclopropyl-5-(4-fluorophenyl)-4-phenyl-3-(p-tolylcarbamoyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate
AS-21.
White solid, mp 163-165 ° C; R f 0.35 (9:1 Chloroform: Methanol); IR (KBr): 3441,
3228, 3101, 2978, 2941, 1730, 1643, 1491. 1247, 833, 738, 704 cm -1 ; 1 H NMR (300
MHz, CDCl 3 ): δ 0.77 (m, 2H, CH 2 ), 0.99-1.11 (m, 3H, CH 2 & CH), 1.21-1.59 (m,
19H, 2 x CH 2 & 5 x CH 3 ), 1.91 (m, 1H, CH), 2.20-2.37 (m, 5H, CH & 2 x CH 2 ), 3.63
(m, 1H, CH), 4.14 (m, 3H, CH & CH 2 ), 6.84 (s, 1H, NH), 6.99-7.26 (m, 13H, Ar); 13 C
NMR (DEPT): (75 MHz, CDCl 3 ): δ 6.81, 7.54, 7.63, 19.62, 20.84, 28.09, 29.96,
36.01, 37.19, 40.38, 42.50, 65.91, 66.14, 115.32, 115.61, 119.50, 126.46, 128.27,
129.25, 130.42, 132.80, 132.90; MS (m/z): 666 [M + ]; Anal. Calcd for C 41 H 47 FN 2 O 5 :
C, 73.85; H, 7.10; N, 4.20; Found: C, 73.84; H, 7.04; N, 4.22.
Department of Chemistry, Saurashtra University, Rajkot-360005 185