Yavari et al.
1325, 1107 cm-1. Anal. Calcd. for C23H26N3O4SCl (475.97): C,
58.04; H, 5.50; N, 8.82. Found: C, 57.46; H, 5.09; N, 8.55. 6j-
131.9 (C), 134.3 (CH), 135.9 (C), 167.3 (C=O), 169.9 (C=O),
170.5 (C=O), 180.8 (C=S).
1
3
I (60%) H NMR: δ = 1.37 (9H, s, CMe3), 1.59 (3H, d, J =
2-(tert-Butylamino)-2-oxo-1-phenylethyl-2-(3-benzoyl-
thioureido)propanoate (6l). Viscous oil; yield: 0.32 g (73%).
3
7.2, Me), 5.03 (1H, quintet, J = 7.2, CH), 6.00 (1H, s, CH),
3
ν
6.23 (1H, s, NH), 7.38-7.88 (5H, m, 5CH), 7.56 (2H, d, J =
IR (KBr): = 3450, 3325, 3242, 1743, 1658, 1599, 1315,
3
3.0, 2CH), 7.86 (2H, d, J = 3.0, 2CH), 9.07 (1H, s, NH),
1127 cm-1. EI-MS: m/z (%) = 467 (M+, 33), 251 (24), 234 (61),
217 (49), 105 (100), 84 (29), 77 (44), 44 (32). Anal. Calcd. for
C23H27N3O4S (441.52): C, 62.57; H, 6.16; N, 9.52 Found: C,
63.01; H, 6.39; N, 9.25. 6l-I (55%) 1H NMR: δ = 1.37 (9H, s,
CMe3), 1.69 (3H, d, 3J = 7.2, Me), 5.18 (1H, quintet, 3J = 7.2,
CH), 6.04 (1H, s, CH), 6.16 (1H, s, NH), 7.38-7.89 (10H, m,
3
11.08 (1H, d, J = 7.2, NH). 13C NMR: δ = 17.4 (Me), 29.1
(CMe3), 52.3 (CMe3), 54.4 (CH), 75.9 (CH), 127.8 (2CH),
129.1 (2CH), 129.3 (2CH), 129.6 (2CH), 131.7 (C), 134.2 (C),
134.5 (C), 135.3 (C), 166.8 (C=O), 167.3 (C=O), 169.8
(C=O), 180.7 (C=S). EI-MS: m/z (%) = 477 (M+ +1, 13), 476
(M+, 34), 251 (21), 242 (10), 235 (55), 225 (51), 105 (100), 77
3
5CH), 9.07 (1H, s, NH), 11.15 (1H, d, J = 7.2, NH). 13C
1
(41), 57 (38), 44 (34). 6j-II (40%) H NMR: δ = 1.40 (9H, s,
NMR: 17.4 (Me), 29.1 (CMe3), 52.2 (CMe3), 54.4 (CH), 76.8
(CH), 127.7 (2CH), 127.8 (2CH), 129.1 (2CH), 129.3 (2CH),
129.6 (CH), 131.8 (C), 134.2 (CH), 135.7 (C), 167.2 (C=O),
167.3 (C=O), 170.0 (C=O), 180.6 (C=S). 6l-II (45%) 1H
CMe3), 1.68 (3H, d, 3J = 7.2, Me), 5.17 (1H, quintet, 3J = 7.2,
CH), 6.08 (1H, s, CH), 6.41 (1H, s, NH), 7.38-7.88 (5H, m,
5CH), 7.56 (2H, d, 3J = 3.0, 2CH), 7.86 (2H, d, 3J = 3.0, 2CH),
3
3
9.07 (1H, s, NH), 11.12 (1H, d, J = 7.2, NH); 13C NMR: δ =
NMR: δ = 1.43 (9H, m, CMe3), 1.60 (3H, d, J = 7.2, Me),
17.7 (Me), 29.1 (CMe3), 52.3 (CMe3), 54.5 (CH), 76.3 (CH),
127.9 (2CH), 129.2 (2CH), 129.3 (2CH), 129.7 (2CH), 131.8
(C), 134.3 (C), 134.6 (C), 135.4 (C), 166.9 (C=O), 167.3
(C=O), 170.3 (C=O), 180.8 (C=S).
5.05 (1H, quintet, 3J = 7.2, CH), 6.12 (1H, s, CH), 6.37 (1H, s,
NH), 7.38-7.89 (10H, m, 5CH), 9.08 (1H, s, NH), 11.09 (1H,
3
d, J = 7.2, NH); 13C NMR: δ = 17.8 (Me), 29.1 (CMe3), 52.2
(CMe3), 54.5 (CH), 77.0 (CH), 127.8 (2CH), 127.9 (2CH),
129.2 (2CH), 129.4 (2CH), 129.7 (CH), 131.9 (C), 134.3
(CH), 136.0 (C), 167.2 (C=O), 167.4 (C=O), 170.4 (C=O),
180.7 (C=S).
2-(Cyclohexylamino)-2-oxo-1-phenylethyl-2-(3-benzoyl-
thioureido)propanoate (6k). Viscous oil; yield: 0.28 g
ν
(60%); IR (KBr): = 3450, 3325, 3242, 1743, 1658, 1599,
1315, 1127 cm-1. EI-MS: m/z (%) = 467 (M+, 33), 251 (24),
234 (61), 217 (49), 105 (100), 84 (29), 77 (44), 44 (32). Anal.
Calcd. for C25H29N3O4S (467.56): C, 64.22; H, 6.24; N, 8.99.
1-(Cyclohexylamino)-2-methyl-1-oxopropan-2-yl-3-
methyl-2-(3-(4-methylbenzoyl)thioureido) butanoate (6m).
White powder; yield: 0.41 g (89%). m.p.: 110-112 ºC; IR
1
ν
Found: C, 65.01; H, 5.99; N, 9.25. 6k-I (62%) H NMR: δ =
(KBr): = 3444, 3423, 3256, 1737, 1657, 1598, 1335, 1100
3
1.16-1.91 (10H, m, 5CH2), 1.68 (3H, d, J = 7.2, Me), 3.81
cm-1. EI-MS: m/z (%) = 461 (M+, 29), 276 (21), 186 (19), 169
(83), 119 (100), 84 (17), 91 (43), 44 (31). Anal. Calcd. for
C24H35N3O4S (461.62): C, 62.44; H, 7.64; N, 9.10. Found: C,
3
(1H, m, CH), 5.03 (1H, quintet, J = 7.2, CH), 6.13 (1H, s,
3
CH), 6.45 (1H, d, J = 7.8, NH), 7.35-7.89 (10H, m, 5CH),
3
1
3
9.10 (1H, s, NH), 11.15 (1H, d, J = 7.2, NH). 13C NMR: δ =
61.88; H, 7.25; N, 9.29. H NMR: δ = 1.12 (6H, d, J = 6.9,
2Me), 1.10-1.90 (10H, m, 5CH2), 1.64 (3H, s, Me), 1.66 (3H,
s, Me), 2.42 (1H, m, CH), 2.46 (3H, s, Me), 3.73 (1H, m, CH),
17.4 (Me), 25.4 (CH2), 25.8 (2CH2), 33.4 (2CH2), 48.9 (CH),
54.6 (CH), 76.7 (CH), 127.7 (2CH), 127.8 (2CH), 129.1
(2CH), 129.4 (CH), 129.6 (2CH), 131.8 (C), 134.2 (CH),
135.6 (C), 167.1 (C=O), 169.8 (C=O), 170.4 (C=O), 180.7
3
3
4.75 (1H, dd, 3J = 7.0, J = 5.0, CH), 6.35 (1H, d, J = 8.3,
NH), 7.34 (2H, d, 3J = 8.2, 2CH), 7.77 (2H, d, 3J = 8.2, 2CH),
1
3
(C=S); 6k-II (38%) H NMR: δ = 1.16-1.91 (10H, m, 5CH2),
9.08 (1H, s, NH), 11.21 (1H, d, J = 7.0, NH); 13C NMR: δ =
3
1.60 (3H, d, J = 7.2, Me), 3.82 (1H, m, CH), 5.17 (1H,
18.6 (Me), 19.7 (Me), 22.1 (Me), 24.9 (CH2), 25.3 (Me), 25.4
(Me), 25.5 (CH2), 25.9 (CH2), 30.9 (CH), 33.3 (2CH2), 48.9
(CH), 64.7 (CH), 83.5 (C), 128.0 (2CH), 128.9 (2CH), 130.3
(C), 145.4 (C), 167.4 (C=O), 168.8 (C=O), 171.9 (C=O),
181.4 (C=S).
quintet, 3J = 7.2, CH), 6.19 (1H, s, CH), 6.59 (1H, d, 3J = 7.8,
NH), 7.35-7.89 (10H, m, 5CH), 9.09 (1H, s, NH), 11.11(1H, d,
3J = 7.2, NH). 13C NMR: δ = 17.8 (Me), 25.3 (CH2), 25.9
(2CH2), 33.5 (2CH2), 49.0 (CH), 54.6 (CH), 78.3 (CH), 127.8
(2CH), 127.9 (2CH), 129.1 (2CH), 129.5 (CH), 129.7 (2CH),
1-(Cyclohexylamino)-2-methyl-1-oxopropan-2-yl-2-(3-
639