Download (6Mb) - Etheses - Saurashtra University

Chapter-5
Synthesis of highly substituted pyrroles
13 C NMR: (100 MHz, CDCl 3 ): δ 19.68, 21.50, 21.67, 26.07, 28.09, 29.93, 35.96,
38.07, 40.91, 42.45, 65.90, 66.39, 98.69, 114.88, 115.29, 115.50, 120.61, 121.77,
126.70, 128.09, 128.12, 128.25, 128.43, 128.64, 128.93, 130.55, 133.14,
133.22,134.62, 137.04, 141.93, 161.06, 163.52, 164.68, 170.20; MS (m/z): 688 [M + ];
Anal. Calcd for C 40 H 46 ClFN 2 O 5 : C, 69.70; H, 6.73; N, 4.06; Found: C, 69.70; H, 6.74;
N, 4.09.
tert-butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-4-((4-fluorophenyl)carbamoyl)-5-
isopropyl-3-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate
AS-14. White solid, mp 170-172 ° C; R f 0.48 (9:1 Chloroform: Methanol); IR (KBr):
3437, 3039, 2985, 2948, 2865, 1739, 1675, 1563, 1549, 1486, 1281, 1087, 1048, 837,
787, 744, 716 cm -1 ; MS (m/z): 672 [M + ]; Anal. Calcd for C 40 H 46 F 2 N 2 O 5 : C, 71.41; H,
6.89; N, 4.16; Found: C, 71.41; H, 6.84; N, 4.19.
tert-butyl 2-((4R,6R)-6-(2-(3-((4-ethylphenyl)carbamoyl)-5-(4-fluorophenyl)-2-
isopropyl-4-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate
AS-15. White solid, mp 202-204 ° C; R f 0.55 (9:1 Chloroform: Methanol); IR (KBr):
3429, 3039, 2975, 2954, 2895, 1736, 1665, 1571, 1542, 1461, 1287, 1081, 1043, 831,
784, 739, 713 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, 73.81; H, 7.54; N, 4.10.
tert-butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-isopropyl-4-((4-nitrophenyl)
carbamoyl)-3-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate
AS-16. White solid, mp 188-190 ° C; R f 0.48 (9:1 Chloroform: Methanol); IR (KBr):
3427, 3045, 2969, 2956, 2875, 1729, 1678, 1581, 1557, 1464, 1271, 1097, 1045, 839,
781, 758, 721 cm -1 ; MS (m/z): 699 [M + ]; Anal. Calcd for C 40 H 46 FN 3 O 7 : C, 68.65; H,
6.63; N, 6.00; Found: C, 68.86; H, 6.64; N, 6.05.
tert-butyl 2-((4R,6R)-6-(2-(3-((2,5-dimethylphenyl)carbamoyl)-5-(4-fluorophenyl)
-2-isopropyl-4-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate
AS-17. White solid, mp 157-159 ° C; R f 0.41 (9:1 Chloroform: Methanol); IR (KBr):
3415, 3048, 2979, 2948, 2875, 1739, 1678, 1579, 1555, 1464, 1276, 1071, 1049, 876,
849, 765, 749, 716 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.
Department of Chemistry, Saurashtra University, Rajkot-360005 184