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Chapter-5
Synthesis of highly substituted pyrroles
tert-butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-isopropyl-4-((4-methoxyphenyl)-
carbamoyl)-3-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate
AS-12. White solid, mp 174-176 ° C; R f 0.45 (9:1 Chloroform: Methanol); IR (KBr):
3412, 3031, 2989, 2935, 2868, 1737, 1671, 1558, 1554, 1474, 1298, 1087, 1047, 845,
775, 734, 703 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ 1.06 (m, 1H, CH), 1.30-1.65 (m,
24H, CH, CH 2 & 7 x CH 3 ), 2.25-2.37 (m, 2H, CH 2 ), 3.54 (m, 3H, CH), 3.73 (m, 5H,
CH 3 & 2 x CH), 4.14 (m, 2H, CH 2 ), 6.72-6.75 (d, 3H, J=7.5Hz, Ar), 6.99 (s, 4H, Ar),
7.16 (s, 7H, Ar & NH); 13 C NMR (DEPT): (75 MHz, CDCl 3 ): δ 19.68, 21.64, 21.82,
26.10, 28.09, 29.92, 35.97, 38.09, 40.79, 42.46, 65.90, 66.41, 113.86, 115.22, 115.50,
121.47, 126.45, 128.29, 130.46, 133.14, 133.25; MS (m/z): 684 [M + ]; Anal. Calcd for
C 41 H 49 FN 2 O 6 : C, 71.91; H, 7.21; N, 4.09; Found: C, 71.94; H, 7.26; N, 4.09.
tert-butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(p-tolylcarbamoyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate
AS-11.
White solid, mp 158-160 ° C; R f 0.47 (9:1 Chloroform: Methanol); IR (KBr): 3477,
3037, 2987, 2939, 2878, 1735, 1651, 1567, 1529, 1474, 1291, 1082, 1037, 837, 798,
731, 704 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ 1.02-1.10 (m, 1H, CH), 1.30-1.66 (m,
24H, CH, CH 2 & 7 x CH 3 ), 2.24-2.42 (m, 5H, CH 2 & CH 3 ), 3.53-3.84 (m, 3H, CH &
CH 2 ), 4.07-4.16 (m, 2H, 2 x CH), 6.80 (s, 1H, NH), 6.98-7.26 (m, 13H, Ar); 13 C
NMR (DEPT): (75 MHz, CDCl 3 ): δ 19.68, 20.83, 21.62, 21.80, 26.09, 28.09, 29.93,
35.97, 38.09, 40.82, 42.46, 65.90, 66.41, 115.22, 115.51, 119.63, 126.48, 128.31,
129.19, 130.47, 133.14, 133.25; MS (m/z): 668 [M + ]; Anal. Calcd for C 41 H 49 FN 2 O 5 :
C, 73.63; H, 7.38; N, 4.19; Found: C, 73.64; H, 7.36; N, 4.19.
tert-butyl 2-((4R,6R)-6-(2-(3-((4-chlorophenyl)carbamoyl)-5-(4-fluorophenyl)-2-
isopropyl-4-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate.
AS-13. White solid, yield 94%, mp 184-186 ° C; R f 0.46 (9:1 Chloroform: Methanol);
IR (KBr): 3410, 3041, 2992, 2943, 2875, 1744, 1677, 1474, 1287, 1075, 1047, 846
cm -1 ; 1 H NMR (400 MHz, CDCl 3 ): δ 0.92-1.01 (m, 1H, CH), 1.22 (s, 3H, CH 3 ), 1.26-
1.28 (m, 4H, CH & CH 3 ), 1.35-137 (s, 9H, 3 x CH 3 ), 1.43-1.45 (d, 6H, 2 x CH 3 ),
1.56-1.60 (m, 2H, CH 2 ), 2.07-2.18 (dd, 1H, CH), 2.27-2.33 (dd, 1H, CH), 3.48-3.53
(m, 1H, CH), 3.60-3.62 (m, 1H, CH), 3.73-3.76 (m, 1H, CH), 3.96-4.09 (m, 2H, CH 2 ),
6.76 (s, 1H, NH), 6.88-6.92 (m, 4H, Ar), 7.02-7.18 (m, 9H, Ar & NH);
Department of Chemistry, Saurashtra University, Rajkot-360005 183