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Chapter-5
Synthesis of highly substituted pyrroles
tert-butyl 2-((4R,6R)-6-(2-(2-cyclopropyl-5-(4-fluorophenyl)-3-((4-methoxyphenyl)carbamoyl)-4-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)
acetate AS-22. White solid, mp 163-165 ° C; R f 0.35 (9:1 Chloroform: Methanol); IR
(KBr): 3421, 3045, 2975, 2948, 2852, 1742, 1664, 1569, 1567, 1461, 1291, 1079,
1041, 851, 781, 745, 714 cm -1 ; MS (m/z): 682 [M + ]; Anal. Calcd for C 41 H 47 FN 2 O 6 : C,
72.12; H, 6.94; N, 4.10; Found: C, 72.12; H, 6.95; N, 4.12.
tert-butyl 2-((4R,6R)-6-(2-(3-((4-chlorophenyl)carbamoyl)-2-cyclopropyl-5-(4-
fluorophenyl)-4-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)
acetate AS-23. White solid, mp 193-194 ° C; R f 0.45 (9:1 Chloroform: Methanol); IR
(KBr): 3452, 3052, 2987, 2939, 2884, 1753, 1679, 1564, 1559, 1482, 1267, 1065,
1039, 856 cm -1 ; MS (m/z): 686 [M + ]; Anal. Calcd for C 40 H 44 ClFN 2 O 5 : C, 69.91; H,
6.45; N, 4.08; Found: C, 69.95; H, 6.48; N, 4.12.
tert-butyl 2-((4R,6R)-6-(2-(2-cyclopropyl-5-(4-fluorophenyl)-3-((4-fluorophenyl)
carbamoyl)-4-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate
AS-24. White solid, mp 172-174 ° C; R f 0.38 (9:1 Chloroform: Methanol); IR (KBr):
3499, 3052, 2975, 2957, 2854, 1742, 1665, 1572, 1556, 1478, 1271, 1073, 1053, 831,
782, 754, 726 cm -1 ; MS (m/z): 670 [M + ]; Anal. Calcd for C 40 H 44 F 2 N 2 O 5 : C, 71.62; H,
6.61; N, 4.18; Found: C, 71.63; H, 6.58; N, 4.12.
tert-butyl 2-((4R,6R)-6-(2-(2-cyclopropyl-3-((4-ethylphenyl)carbamoyl)-5-(4-
fluorophenyl)-4-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)
acetate AS-25. White solid, mp 112-115 ° C; R f 0.45 (9:1 Chloroform: Methanol); IR
(KBr): 3438, 3043, 2965, 2943, 2887, 1736, 1645, 1562, 1532, 1456, 1272, 1061,
1031, 821, 774, 729, 703 cm -1 ; MS (m/z): 680 [M + ]; Anal. Calcd for C 42 H 49 FN 2 O 5 : C,
74.09; H, 7.25; N, 4.11; Found: C, 74.13; H, 7.28; N, 4.12.
tert-butyl 2-((4R,6R)-6-(2-(2-cyclopropyl-5-(4-fluorophenyl)-3-((4-nitrophenyl)-
carbamoyl)-4-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate
AS-26. White solid, mp 132-134 ° C; R f 0.52 (9:1 Chloroform: Methanol); IR (KBr):
3413, 3052, 2972, 2961, 2865, 1739, 1688, 1571, 1562, 1476, 1269, 1084, 1051, 842,
778, 768, 728 cm -1 MS (m/z): 697 [M + ]; Anal. Calcd for C 40 H 44 FN 3 O 7 : C, 68.85; H,
6.36; N, 6.02; Found: C, 68.87; H, 6.38; N, 6.08.
Department of Chemistry, Saurashtra University, Rajkot-360005 186