Med Chem Res (2014) 23:3144–3156
3153
CH3CHCONH–), 4.21–3.61 (m, 4H, 29–OCH2CH3), 2.31
(s, 3H, H-11), 1.61 (d, J = 6.7 Hz, 3H, –CH(CH3) CONH–),
1.30 (t, J = 7.0 Hz, 3H, –OCH2CH3), 1.08 (t, J = 7.0 Hz,
3H, –OCH2CH3). 13C NMR (125 MHz, CDCl3) d 170.42
(C=O), 160.91 (C-2), 159.72 (C-7), 154.52 (C-4), 152.13
(C-9), 135.56 (C-20), 133.96 (C-90), 131.36 (C-100), 129.27
(C-30), 128.46 (C-60), 127.86 (C-80), 127.61 (C-5), 127.09
(C-40), 126.49 (C-10), 126.31 (C-70), 125.19 (C-50), 114.60
(C-10), 113.58 (C-3), 111.98 (C-6), 106.66 (C-8), 79.03
(–CHCONH–), 63.81 (–OCH2CH3), 63.65 (–OCH2CH3),
58.36 (PhCH–), 18.69 (C-11), 18.52 (–CH(CH3) CONH–),
16.34 (–OCH2CH3), 16.23 (–OCH2CH3). 31P NMR
(202 MHz, CDCl3) d 20.86. HRMS for C28H31NO7P
([M?H]?): calcd 524.18381; found 524.18296.
5), 126.09 (C-40), 114.75 (C-10), 112.75 (C-3), 112.43 (C-6),
103.30 (C-8), 75.63 (–CHCONH–), 63.23 (–OCH2CH3),
63.07 (–OCH2CH3), 35.95 (–PhCCH2CH2CH3), 18.62
(–PhCCH2CH2CH3), 18.53 (C-11), 17.51 (–CH(CH3)CONH–),
17.47 (–PhCCH2CH2CH3), 16.27 (–OCH2CH3), 16.21
(–OCH2CH3), 14.19 (–PhCCH2CH2CH3). 31P NMR (202
MHz, CDCl3) d 23.21. ESI–MS m/z: 516.2 (M?H)?. HRMS
for C27H35NO7P ([M?H]?): calcd 516.21511; found
516.21431.
Diethyl1-((S)2-(4-methyl-2-oxo-2H-chromen-7-
yloxy)propanamido)-1-phenylpropylphosphonate (8p)
Yield 73 %. Light yellow solid. m.p.126.8–128.8 °C. 1H
NMR (500 MHz, CDCl3) d 7.46 (d, J = 8.8 Hz, 1H, H-5),
7.42–7.11 (m, 5H, –CC6H5), 6.98 (dd, J = 9.3, 2.5 Hz, 1H,
H-6), 6.63 (d, J = 2.5 Hz, 1H, H-8), 6.04 (s, 1H, H-3), 4.76 (q,
J = 6.6 Hz, 1H, –CH(CH3)CONH–), 4.19–4.07 (m, 2H,
C6H5CH2–), 4.03–3.51 (m, 4H, 29–OCH2CH3), 2.27 (s, 3H,
H-11), 1.50 (d, J = 6.7 Hz, 3H, CH3CHCONH–), 1.12 (q,
J = 6.7 Hz, 2H, –CCH2CH3), 1.27 (t, J = 7.1 Hz, 3H, 29
–OCH2CH3), 1.15 (d, J = 6.7 Hz, 3H, –OCH2CH3),0.95 (t,
J = 7.1 Hz, 3H, –CCH2CH3). 13C NMR (125 MHz, CDCl3) d
170.52 (C=O), 1601.21 (C-2), 157.46 (C-7), 155.63 (C-4),
153.30 (C-9), 135.06 (C-10), 128.46 (C-30,50), 128.06 (C-20,60),
127.16 (C-5), 126.24 (C-40), 114.25 (C-10), 112.65 (C-3),
112.34 (C-6), 103.26 (C-8), 76.43 (–CHCONH–), 63.24
(–OCH2CH3), 63.08 (–OCH2CH3), 45.56 (–PhCH2CCH2
CH3), 30.06 (–PhCH2CCH2CH3), 18.62 (C-11), 18.53
(–PhCH2CCH2CH3), 17.51 (–CH(CH3)CONH–), 16.24
(–OCH2CH3), 16.10 (–OCH2CH3), 13.56 (–PhCH2
CCH2CH3). 31P NMR (202 MHz, CDCl3) d 20.46. HRMS for
C27H35NO7P ([M?H]?): calcd 516.21511; found 516.21462.
Diethyl1-((S)2-(4-methyl-2-oxo-2H-chromen-7-
yloxy)propanamido)-1-phenylethylphosphonate (8n)
Yield 78 %. Light yellow solid. m.p.61.9–63.9 °C. 1H NMR
(500 MHz, CDCl3) d 7.54 (d, J = 8.8 Hz, 1H, H-5),
7.44–7.20 (m, 5H, –CC6H5), 6.92 (dd, J = 8.7, 2.5 Hz, 1H,
H-6), 6.89 (d, J = 2.2 Hz, 1H, H-8), 6.18 (s, 1H, H-3), 4.60
(q, J = 6.6 Hz, 1H, –CH(CH3)CONH–), 3.86–3.53 (m, 4H,
29–OCH2CH3), 2.41 (s, 3H, H-11), 2.06 (d, J = 6.2 Hz, 3H,
CH3CHCONH–), 1.63 (d, J = 6.7 Hz, 3H, C6H5CCH3),
1.28 (t, J = 7.0 Hz, 3H, –OCH2CH3), 1.08 (t, J = 7.0 Hz,
3H, –OCH2CH3). 13C NMR (125 MHz, CDCl3) d 170.16
(C=O), 160.65 (C-2), 159.70 (C-7), 155.04 (C-4), 152.05 (C-
9), 137.57 (C-10), 128.90 (C-30,50), 128.71 (C-20,60), 127.97
(C-5), 126.69 (C-40), 114.73 (C-10), 112.82 (C-3), 112.25
(C-6), 103.27 (C-8), 75.53 (–CHCONH–), 63.72 (–OCH2
CH3), 63.56 (–OCH2CH3), 58.40 (PhC(CH3)–), 21.12
(C-11), 18.67 (–CH(CH3)CONH–), 18.44 (PhC(CH3)–),
16.21 (–OCH2CH3), 16.11 (–OCH2CH3). 31P NMR
(202 MHz, CDCl3) d 23.90. HRMS for C25H31NO7P
([M?H]?): calcd 488.18381; found 488.18259.
Diethyl1-((S)2-(4-methyl-2-oxo-2H-chromen-7-
yloxy)propanamido)-1-(4-chlorophenyl)ethylphosphonate
(8q)
Diethyl1-((S)2-(4-methyl-2-oxo-2H-chromen-7-
1
yloxy)propanamido)-1-phenylbutylphosphonate (8o)
Yield 75 %. Light yellow solid. m.p.128.2–130.2 °C. H
NMR (500 MHz, CDCl3) d 7.56 (d, J = 8.7 Hz, 1H,
H-5), 7.39–7.30 (m, 4H, –CC6H4Cl), 6.94–6.90 (dd,
J = 7.4, 2.5 Hz, 1H, H-6), 6.89 (d, J = 2.5 Hz, 1H,
H-8), 6.19 (s, 1H, H-3), 4.74–4.66 (q, J = 6.6 Hz, 1H,
–CH(CH3)CONH–), 4.03–3.61 (m, 4H, 29–OCH2CH3),
2.42 (s, 3H, H-11), 2.04 (d, J = 6.7 Hz, 3H, –CH(CH3)
CONH–), 1.62 (d, J = 6.9 Hz, 3H, –C6H5CCH3), 1.17
(t, J = 7.1 Hz, 3H, –OCH2CH3), 1.08 (t, J = 7.1 Hz,
3H, –OCH2CH3). 13C NMR (125 MHz, CDCl3) d
170.10 (C=O), 160.48 (C-2), 159.46 (C-7), 154.88
(C-4), 152.13 (C-9), 136.53 (C-10), 130.45 (C-40),
128.33 (C-30,50), 128.22 (C-20,60), 127.63 (C-5), 114.81
(C-10), 112.92 (C-3), 112.17 (C-6), 103.27 (C-8), 75.64
Yield 70 %. Light yellow solid. m.p.134.9–136.9 °C. 1H
NMR (500 MHz, CDCl3) d 7.52 (d, J = 8.8 Hz, 1H, H-5),
7.39–7.09 (m, 5H, –CC6H5), 6.95 (dd, J = 9.3, 2.5 Hz, 1H,
H-6), 6.87 (d, J = 2.5 Hz, 1H, H-8), 6.11 (s, 1H, H-3), 4.76 (q,
J = 6.6 Hz, 1H, –CH(CH3)CONH–), 3.93–3.33 (m, 4H, 29
–OCH2CH3), 2.49–2.40 (m, 2H, –CCH2), 2.35 (s, 3H, H-11),
1.63 (d, J = 6.7 Hz, 3H, –CH(CH3)CONH–), 1.53–1.18 (m,
2H, –CH2CH2CH3), 1.12 (d, J = 6.7 Hz, 3H, –OCH2CH3),
0.99 (t, J = 7.1 Hz, 3H, –OCH2CH3), 0.83 (t, J = 7.3 Hz, 3H,
–CH2CH2CH3). 13C NMR (125 MHz, CDCl3) d 170.14
(C=O), 160.81 (C-2), 159.69 (C-7), 155.03 (C-4), 152.30 (C-
9), 137.64 (C-10), 128.45(C-30,50), 128.12 (C-20,60), 127.58(C-
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