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K. Koran et al.
complete, the mixture was slowly poured into water (50 mL) and reprecipitated
twice from water. A white solid 7 was obtained (0.34 g, 73 %). Anal. Calcd. for
C83H68O23N9P3, (MW = 1652.40). C, 60.33; H, 4.15; N, 7.63 %. Found: C, 60.02;
H, 3.99; N, 7.45 %. IR (cm-1): 3285 mOH, 1746 mC=O, 1189 mP=N, 3010, 3065
m
C–H(Ar), 2972, 2938, 2603 mC–H (Aliphatic), 1508, 1599, 1583, 1610 mC=N, C=C, 950
1
mP–O–C.
31P NMR: 8.50(s). H NMR: 10.61 (1H, s, H(14)), 7.15–7.99 (33 H, m,
H(3), H(30), H(5), H(50), H(6), H(60), H(11), H(12), H(13)), 3.76–3,78 (18 H, s,
H(7), H(70)), 8.82–8,79 (6 H, s, H(8), H(80)), 2.45 and 3.32 (DMSO-d). 13C NMR:
167.60 C(9), 157.46 C(8), 157.41 C(80), 150.85 C(1), 150.82 C(10), 142.77 C(2),
142.73 C(20), 133.13 C(13), 131.02 C(10), 129.50 C(11), 129.18 C(12), 128.83
C(4), 128.80 C(40), 121.72 C(5), 121.69 C(50), 118.60 C(6), 118.58 C(60), 111.47
C(3), 111.44 C(30), 56.59 C(7), 56.09 C(70), 39.97 (DMSO-d).
Reaction of 3 with propanoyl chloride
A solution of propanoyl chloride (0.35 mL, 0.35 g, 4.0 mmol) in THF (10 mL) was
slowly added dropwise to a stirred and cooled (0–5 °C) mixture of 3 (0.4 g,
0.35 mmol) and triethylamine (0.60 mL, 0.42 g, 4.24 mmol) in THF (30 mL). The
reaction was performed at room temperature for 48 h. When the reaction was
complete, the mixture was slowly poured into water (50 mL) and reprecipitated
twice from water. A white solid 8 was obtained (0.39 g, 76 %). Anal. Calcd. for
C66H72O24N9P3, (MW = 1468.24). Calcd.: C, 53.99; H, 4.94; N: 8.59 %. Found: C,
53.52; H, 4.61; N, 8.27 %. IR (cm-1): 1764 mC=O, 1190 mP=N, 3000, 3070 mC–H(Ar)
,
2980, 2941 mC–H (Aliphatic), 1509, 1598, 1584 mC=N, C=C, 950 mP–O–C
.
31P NMR:
1
8.55(s). H NMR: 8.53 (6 H, s, H(8)), 6.95–7.30 (18 H, m, H(3), H(5), H(6)), 2.5
(12 H, m, H(10)), 2.13–3.81 (18 H, s, H(7)), 1.00–1.18 (18 H, t, H(11)), 2.47 and
3.32 (DMSO-d). 13C NMR: 171.60 C(9), 155.99 C(8), 150.77 C(1), 141.72 C(2),
137.34 C(4), 128.05 C(5), 121.40 C(6), 111.33 C(3), 56.50 C(7), 25.70 C(10), 9.10
C(11), 39.97 (DMSO-d).
Reaction of 3 with 4-methoxybenzoyl chloride
A solution of 4-methoxybenzoyl chloride (0.45 g, 2.65 mmol) in acetone (10 mL)
was slowly added dropwise to a stirred and cooled (0–5 °C) mixture of 3 (0.4 g,
0.35 mmol) and K2CO3 (0.58 g, 4.24 mmol) in acetone (30 mL). The reaction was
performed at room temperature for 48 h. When the reaction was complete, the
precipitate was isolated by filtration and the solvent was removed. The product was
dissolved in a very small amount of acetone and was precipitated with hexane. The
solvent was removed under vacuum over 96 h. A white solid 9 was obtained
(0.54 g, 79 %). Anal. Calcd. for C96H84O30N9P3, (MW = 1936.66). C, 59.54; H,
4.37; N, 6.51 %. Found: C, 59.06; H, 4.08; N, 6.12 %. IR (cm-1): 1789 mC=O, 1190
m
P=N, 3010, 3065 mC–H(Ar), 2930, 2845 mC–H (Aliphatic), 1606, 1579, 1510 mC=N, C=C,
1
950 mP–O–C.
31P NMR: 8.62(s). H NMR: 8.74 (6 H, s, H(8)), 3.84 (18 H, s, H(7)),
3.78 (18 H, s, H(14)), 6.94–8.04 (42 H, m, H(3), H(5), H(6), H(11), H(12)), 2.44 and
3.33 (DMSO-d). 13C NMR: 167.31 C(9), 163.25 C(13), 156.97 C(8), 150.82 C(1),
123