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Chapter-5
Synthesis of highly substituted pyrroles
tert-butyl 2-((4R,6R)-6-(2-(3-((4-chlorophenyl)carbamoyl)-5-(4-fluorophenyl)-2-
methyl-4-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate AS-
03. White solid, mp 147-149 ° C; R f 0.47 (9:1 Chloroform: Methanol); IR (KBr): 3458,
3035, 2988, 2932, 2881, 1731, 1675, 1564, 1547, 1486, 1291, 1087, 1037, 841 cm -1 ;
MS (m/z): 660 [M + ]; Anal. Calcd for C 38 H 42 ClFN 2 O 5 : C, 69.03; H, 6.40; N, 4.24;
Found: C, 69.05; H, 6.42; N, 4.28.
tert-butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-4-((4-fluorophenyl)carbamoyl)-5-
methyl-3-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate AS-
04. White solid, mp 153-155 ° C; R f 0.52 (9:1 Chloroform: Methanol); IR (KBr): 3411,
3030, 2979, 2937, 2879, 1725, 1660, 1560, 1535, 1473, 1290, 1095, 1031, 833, 790,
735, 705 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ 1.03-1.07 (m, 1H, CH), 1.30-1.63 (m,
18H, CH 2 , CH & 5 x CH 3 ), 2.24-2.37 (m, 2H, CH 2 ), 2.71 (s, 3H, CH 3 ), 3.66 (m, 1H,
CH), 3.86-3.99 (m, 2H, CH 2 ), 4.14-4.17 (m, 1H, CH), 6.83-7.00 (m, 7H, Ar), 7.12-
7.28 (m, 7H, Ar & NH); 13 C NMR (DEPT): (75 MHz, CDCl 3 ): δ 11.61, 19.62. 28.09,
29.96, 36.05, 37.16, 40.23, 42.46, 65.88, 65.96, 115.11, 115.26, 115.41, 115.54,
120.66, 120.77, 127.31, 128.66, 131.16, 132.84, 132.95; MS (m/z): 644 [M + ]; Anal.
Calcd for C 38 H 42 F 2 N 2 O 5 : C, 70.79; H, 6.57; N, 4.34; Found: C, 70.75; H, 6.52; N,
4.38.
tert-butyl 2-((4R,6R)-6-(2-(3-((4-ethylphenyl)carbamoyl)-5-(4-fluorophenyl)-2-
methyl-4-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate AS-
05. White solid, mp 172-174 ° C; R f 0.54 (9:1 Chloroform: Methanol); IR (KBr): 3402,
3063, 2995, 2974, 2875, 1724, 1660, 1533, 1255, 842, 734, 705 cm -1 ; 1 H NMR (300
MHz, CDCl 3 ): δ ppm 1.16-1.18 (m, 4H, CH & CH 3 ), 1.31-1.76 (m, 18H, CH, CH 2 &
5 x CH 3 ), 2.21-2.36 (m, 2H, CH 2 ), 2.53-2.55 (m, 2H, CH 2 ), 2.71 (s, 3H, CH 3 ), 3.66
(m, 1H, CH), 3.89-3.97 (m, 2H, CH 2 ), 4.17 (m, 1H, CH), 6.91-6.99 (m, 7H, Ar),
7.14-7.26 (m, 7H, Ar & NH); 13 C NMR (DEPT): (75 MHz, CDCl 3 ): δ 11.61, 15.72.
19.62, 28.09, 28.25, 29.97, 36.05, 37.18, 40.20, 42.48, 65.89, 65.98, 115.23, 115.51,
120.66, 119.30, 128.03, 128.62, 131.15, 132.87, 132.97; MS (m/z): 654 [M + ]; Anal.
Calcd for C 40 H 47 FN 2 O 5 : C, 73.37; H, 7.23; N, 4.28; Found: C, 73.35; H, 7.25; N, 4.28.
Department of Chemistry, Saurashtra University, Rajkot-360005 181