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(m, 8H), 7.23 (d, J=8.0 Hz, 2H), 6.00 (d, J=8.0 Hz, 1H), 4.93 (s, 2H),
4.83–4.78 (m, 1H), 3.32–2.85 (m, 2H), 2.18 (t, J=7.0 Hz, 2H), 2.13–
1.84 (m, 2H), 1.61–1.59 (m, 4H), 1.45 (s, 9H), 1.30–1.28 ppm (m,
4H); 13C NMR (100 MHz, CDCl3): d=172.48, 170.93, 169.30, 140.67,
139.76, 135.45, 135.26, 129.87, 129.16, 128.74, 128.64, 128.56,
127.23, 127.00, 126.93, 82.46, 78.03, 53.28, 37.65, 36.20, 32.73,
28.72, 28.26, 27.95, 25.14, 24.94 ppm.
Methyl (2S)-2-[[8-[benzyloxy-(3-methoxy-3-oxo-propyl)amino]-8-
oxo-octanoyl]amino]-3-(4-phenylphenyl)propanoate (15n). The
title compound was prepared following the same procedure used
for the synthesis of 15i, using 14c (87.7 mg, 0.24 mmol) instead of
14a and 5 (70.0 mg, 0.24 mmol) instead of 9b; yield=50%.
1H NMR (400 MHz, CDCl3): d=7.60–7.53 (m, 4H), 7.50–7.30 (m, 8H),
7.18 (d, J=7.5 Hz, 2H), 6.07 (d, J=7.0 Hz, 1H), 5.06–4.87 (m, 1H),
4.80 (s, 2H), 4.03–3.92 (m, 2H), 3.76 (s, 3H), 3.63 (s, 3H), 3.21 (dd,
J=14.0, 5.5 Hz, 1H), 3.14 (dd, J=14.0, 6.0 Hz, 1H), 2.59 (t, J=
6.5 Hz, 2H), 2.46–2.31 (m, 2H), 2.27–2.10 (m, 2H), 1.64–1.58 (m,
4H), 1.44–1.13 ppm (m, 4H); 13C NMR (100 MHz, CDCl3): d=175.55,
172.75, 172.20, 170.30, 140.62, 139.96, 134.99, 134.31, 129.71,
129.33, 129.01, 128.80, 128.71, 127.32, 127.25, 126.99, 76.33, 52.96,
52.39, 51.81, 41.46, 37.51, 36.36, 32.29, 31.94, 28.92, 28.89, 25.37,
24.22 ppm.
tert-Butyl (2S)-2-[[8-(benzyloxyamino)-8-oxo-octanoyl]amino]-3-
phenyl-propanoate (15j). The title compound was prepared fol-
lowing the same procedure used for the synthesis of 15i, using 5
(90.4 mg, 0.31 mmol) instead of 9b; yield=71%. 1H NMR
(400 MHz, DMSO): d=10.93 (s, 1H), 8.14 (d, J=8.0 Hz, 1H), 7.44–
7.31 (m, 5H), 7.31–7.17 (m, 5H), 4.78 (s, 2H), 4.40–4.30 (m, 1H),
2.96 (dd, J=14.0, 6.0 Hz, 1H), 2.85 (dd, J=14.0, 9.0 Hz, 1H), 2.04 (t,
J=7.0 Hz, 2H), 1.92 (t, J=7.0 Hz, 2H), 1.49–1.37 (m, 4H), 1.33 (s,
9H), 1.18–1.38 ppm (m, 4H); 13C NMR (100 MHz, DMSO): d=172.52,
171.31, 169.75, 137.84, 136.52, 129.53, 129.16, 128.69, 128.60,
128.52, 126.81, 80.85, 77.12, 54.35, 37.33, 35.37, 32.63, 28.68, 28.60,
27.96, 25.49, 25.24 ppm.
Methyl (2S)-2-[[8-[benzyloxy-(3-tert-butoxy-3-oxo-propyl)amino]-
8-oxo-octanoyl]amino]-3-(4-phenylphenyl)propanoate (15o). The
title compound was prepared following the same procedure used
for the synthesis of 15i, using 14b (126.3 mg, 0.31 mmol) instead
of 14a and 5 (90.4 mg, 0.31 mmol) instead of 9b; yield=60%.
1H NMR (400 MHz, CDCl3): d=7.65–7.52 (m, 4H), 7.49–7.33 (m, 8H),
7.19 (d, J=8.0 Hz, 2H), 5.99 (d, J=8.0 Hz, 1H), 4.96 (m, 1H), 4.83 (s,
2H), 3.93 (t, J=7.0 Hz, 2H), 3.78 (s, 3H), 3.23 (dd, J=14.0, 6.0 Hz,
1H), 3.17 (dd, J=14.0, 6.0 Hz, 1H), 2.55 (t, J=7.0 Hz, 2H), 2.35 (t,
J=7.5 Hz, 2H), 2.21 (t, J=7.5 Hz, 2H), 1.70–1.52 (m, 4H), 1.44 (s,
9H), 1.36–1.25 ppm (m, 4H); 13C NMR (100 MHz, CDCl3): d=175.32,
172.65, 172.13, 170.87, 140.58, 139.95, 134.89, 134.37, 129.66,
129.27, 128.91, 128.75, 128.64, 127.28, 127.22, 126.96, 80.79, 76.30,
52.89, 52.36, 41.51, 37.48, 36.35, 33.12, 32.28, 28.90, 28.86, 28.00,
25.33, 24.20 ppm.
Methyl (2S)-2-[[7-(benzyloxyamino)-7-oxo-heptanoyl]amino]-3-
(4-phenylphenyl)propanoate (15k). The title compound was pre-
pared following the same procedure used for the synthesis of 15i,
using 14d (26.5 mg, 0.1 mmol) instead of 14a and 5 (29.2 mg,
0.1 mmol) instead of 9b; yield=31%. 1H NMR (400 MHz, CDCl3):
d=7.64–7.49 (m, 2H), 7.49–7.31 (m, 10H), 7.18 (d, J=8.0 Hz, 2H),
6.24–5.87 (m, 1H), 5.09–4.70 (m, 3H), 3.76 (s, 3H), 3.34–2.98 (m,
2H), 2.71–2.69 (m, 2H), 2.23–2.17 (m, 2H), 1.79–1.51 (m, 4H), 1.49–
1.16 ppm (m, 2H); 13C NMR (100 MHz, CDCl3): d=172.64, 172.16,
170.75, 140.51, 139.89, 134.88, 133.72, 129.63, 129.19, 128.78,
128.76, 128.56, 127.32, 127.21, 126.92, 78.14, 52.91, 52.40, 37.42,
36.35, 32.63, 28.14, 24.93, 24.59 ppm.
Methyl
3-[benzyloxy-[8-[[(1S)-2-(benzyloxyamino)-2-oxo-1-[(4-
phenylphenyl)methyl]ethyl]amino]-8-oxo-octanoyl]amino]propa-
noate (15p). The title compound was prepared following the
same procedure used for the synthesis of 15i, using 14c (91 mg,
0.25 mmol) instead of 14a and 11 a (115.1 mg, 0.25 mmol) instead
of 9b; yield=73%. 1H NMR (400 MHz, CDCl3): d=8.81 (bs, 1H),
7.60–7.53 (m, 4H), 7.47–7.33 (m, 10H), 7.31–7.22 (m, 5H), 6.23 (d,
J=8.0 Hz, 1H), 4.86 (d, J=11.0 Hz, 1H), 4.81 (s, 2H), 4.72 (d, J=
11.0 Hz, 1H), 4.55–4.50 (m, 1H), 3.98 (t, J=7.0 Hz, 2H), 3.64 (s, 3H),
3.15 (dd, J=14.0, 8.0 Hz, 1H), 3.07 (dd, J=14.0, 6.5 Hz, 1H), 2.60 (t,
J=7.0 Hz, 2H), 2.35 (t, J=7.5 Hz, 2H), 2.14 (t, J=7.5 Hz, 2H), 1.63–
1.49 (m, 4H), 1.36–1.17 ppm (m, 4H); 13C NMR (100 MHz, CDCl3):
d=174.15, 173.36, 170.63, 168.46, 140.50, 139.94, 135.18, 134.86,
134.26, 129.72, 129.26, 129.13, 128.97, 128.77, 128.72, 128.66,
128.50, 127.32, 126.92, 120.65, 78.28, 76.28, 51.97, 51.78, 41.33,
37.20, 36.08, 32.15, 31.91, 28.63, 28.59, 25.11, 24.01 ppm.
Methyl (2S)-2-[[7-[benzyloxy-(3-methoxy-3-oxo-propyl)amino]-7-
oxo-heptanoyl]amino]-3-(4-phenylphenyl)propanoate (15l). The
title compound was prepared following the same procedure used
for the synthesis of 15i using 14 f (89.7 mg, 0.25 mmol) instead of
14a and 5 (72.9 mg, 0.25 mmol) instead of 9b; yield=53%.
1H NMR (400 MHz, CDCl3): d=7.60–7.53 (m, 4H), 7.47–7.36 (m, 8H),
7.18 (d, J=8.0 Hz, 2H), 6.00 (d, J=7.5 Hz, 1H), 4.97–4.92 (m, 1H),
4.80 (s, 2H), 3.97 (t, J=7.0 Hz, 2H), 3.77 (s, 3H), 3.64 (s, 3H), 3.22
(dd, J=14.0, 6.0 Hz, 1H), 3.16 (dd, J=14.0, 6.0 Hz, 1H), 2.59 (t, J=
7.0 Hz, 2H), 2.37 (t, J=7.5 Hz, 2H), 2.21 (t, J=7.5 Hz, 2H), 1.67–1.56
(m, 4H), 1.36–1.29 ppm (m, 2H); 13C NMR (100 MHz, CDCl3): d=
175.39, 172.57, 172.17, 171.93, 140.62, 139.99, 134.96, 134.31,
129.69, 129.34, 129.01, 128.79, 128.71, 127.31, 127.26, 127.00,
76.33, 52.95, 52.37, 51.80, 41.32, 37.51, 36.20, 32.14, 31.91, 28.74,
25.23, 23.90 ppm.
tert-Butyl 3-[benzyloxy-[8-[[(1S)-2-(benzyloxyamino)-2-oxo-1-[(4-
phenylphenyl)methyl]ethyl]amino]-8-oxo-octanoyl]amino]propa-
noate (15q). The title compound was prepared following the
same procedure used for the synthesis of 15i, using 14b
(126.3 mg, 0.31 mmol) instead of 14a and 11 a (142.7 mg,
0.31 mmol) instead of 9b; yield=73%. 1H NMR (400 MHz, CDCl3):
d=9.12 (s, 1H), 7.63–7.49 (m, 4H), 7.47–7.29 (m, 13H), 7.25–7.24
(m, 2H), 6.41 (d, J=7.0 Hz, 1H), 4.85 (d, J=11.0 Hz, 1H), 4.82 (s,
2H), 4.72 (d, J=11.0 Hz, 1H), 4.62–4.53 (m, 1H), 3.92 (t, J=7.0 Hz,
2H), 3.15 (dd, J=13.5, 8.0 Hz, 1H), 3.06 (dd, J=13.5, 7.0 Hz, 1H),
2.54 (t, J=7.0 Hz, 2H), 2.33 (t, J=7.5 Hz, 2H), 2.13 (t, J=7.5 Hz,
2H), 1.62–1.46 (m, 4H), 1.43 (s, 9H), 1.33–1.15 ppm (m, 4H);
13C NMR (100 MHz, CDCl3): d=175.15, 173.45, 170.86, 168.46,
140.51, 139.90, 135.20, 134.88, 134.35, 129.74, 129.25, 129.13,
128.91, 128.76, 128.69, 128.63, 128.47, 127.29, 126.91, 120.65,
Methyl (2S)-2-[[7-[benzyloxy-(3-tert-butoxy-3-oxo-propyl)amino]-
7-oxo-heptanoyl]amino]-3-(4-phenylphenyl)propanoate (15m).
The title compound was prepared following the same procedure
used for the synthesis of 15i, using 14e (200 mg, 0.5 mmol) in-
stead of 14a and 5 (146 mg, 0.5 mmol) instead of 9b; yield=51%.
1H NMR (400 MHz, CDCl3): d=7.69–7.50 (m, 4H), 7.46–7.32 (m, 8H),
7.19–7.17 (m, 2H), 6.04 (d, J=8.0 Hz, 1H), 4.94 (dt, J=8.0, 6.0 Hz,
1H), 4.80 (s, 2H), 3.91 (t, J=7.0 Hz, 2H), 3.76 (s, 3H), 3.21 (dd, J=
14.0, 6.0 Hz, 1H), 3.14 (dd, J=14.0, 6.0 Hz, 1H), 2.53 (t, J=7.0 Hz,
2H), 2.35 (t, J=7.5 Hz, 2H), 2.20 (t, J=7.5 Hz, 2H), 1.66–1.55 (m,
4H), 1.43 (s, 9H), 1.35–1.27 ppm (m, 2H); 13C NMR (100 MHz,
CDCl3): d=175.15, 172.52, 172.11, 170.81, 140.57, 139.91, 134.95,
134.36, 129.63, 129.26, 128.88, 128.73, 128.62, 127.25, 127.19,
126.94, 80.74, 76.28, 52.92, 52.29, 41.55, 37.46, 36.14, 33.09, 32.13,
28.71, 27.99, 25.20, 23.89 ppm.
ChemMedChem 2016, 11, 1 – 22
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