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E to give the product as a yellow light powder (95%
yield). IR nmax (cmꢀ1) 1751, 1721, 1700, 1659 (C¼O).
7.33–7.28 (m, 5H), 6.01 (s, 2H), 5.41 (s, 1H), 5.25 (s,
1H), 5.04 (s, 2H), 3.90 (t, 1H, J=6.6 Hz), 3.82 (s, 2H),
2.96 (d, 2H, J=6.7 Hz), 1.46 (s, 9H). 13C NMR(CDCl 3,
100 MHz) d 172.74, 168.99, 153.92, 137.49, 128.37,
127.88, 127.76, 81.49, 66.56, 52.91, 45.01, 41.61, 27.92.
MS (FAB+) 352.2 (MH+).
1H NMR(CDCl , 400 MHz) d 7.75 (d, 2H, J=7.6 Hz),
3
7.59 (d, 2H, J=7.6 Hz), 7.41–7.34 (m, 9H), 6.44 (s, 1H),
5.43 (s, 1H), 5.10 (s, 2H), 4.95 (s, 1H), 4.45–4.37 (m,
3H), 4.24 (t, 1H, J=6.3 Hz), 3.90 (s, 2H), 3.04 (d, 2H,
J=5.9 Hz), 1.44 (s, 9H). 13C NMR(CDCl 3, 100 MHz) d
171.02, 168.83, 157.40, 156.38, 145.09, 141.13, 137.89,
128.43, 128.28, 127.67, 127.09, 126.88, 125.08, 119.74,
81.29, 66.87, 64.23, 52.94, 47.04, 45.61, 30.34, 27.98. MS
(FAB+) 574.2 (MH+). Mp (ꢁC) 118.
Nꢀ-Carbobenzyloxy-2,4-diamino-L-butyrylglycine tert-
butyl ester (2f). This compound was prepared using
general procedure F to give the product as a light yellow
viscous solid (92% yield). IR nmax (cmꢀ1) 3054 (NH2);
1747, 1725, 1666 (C¼O). 1H NMR(CDCl 3, 400 MHz) d
7.33–7.29 (m, 5H), 6.02 (s, 2H), 5.45 (s, 1H), 5.27 (s,
1H), 5.03 (s, 2H), 3.94 (t, 1H, J=6.7 Hz), 3.82 (s, 2H),
2.96 (t, 2H, J=4.7 Hz), 1.93 (td, 2H, J=6.8 Hz, J=4.7
Hz), 1.48 (s, 9H). 13C NMR(CDCl 3, 100 MHz) d
172.67, 168.84, 156.47, 136.45, 128.32, 127.86, 127.76,
81.47, 66.51, 52.81, 44.90, 41.77, 34.88, 27.81. MS
(FAB+) 366.2 (MH+).
Nꢀ-Carbobenzyloxy-2-amino-Nꢁ-9-fluorenylmethoxycar-
bonyl-4-diamino-L-butyrylglycine tert-butyl ester (2e).
This compound was prepared using general procedure
E to give the product as a yellow light powder (96%
yield). IR nmax (cmꢀ1) 1752, 1720, 1702, 1659 (C¼O).
1H NMR(CDCl , 400 MHz) d 7.77 (d, 2H, J=7.6 Hz),
3
7.61 (d, 2H, J=7.6 Hz), 7.41–7.32 (m, 9H), 6.44 (s, 1H),
5.45 (s, 1H), 5.11 (s, 2H), 4.95 (s, 1H), 4.44–4.35 (m,
3H), 4.22 (t, 1H, J=6.1 Hz), 3.91 (s, 2H), 3.03 (t, 2H,
J=5.4 Hz), 1.71 (td, 2H, J=6.2 Hz, J=5.4 Hz), 1.41 (s,
9H). 13C NMR(CDCl 3, 100 MHz) d 172.01, 168.82,
157.12, 156.40, 143.98, 141.22, 136.35, 128.48, 128.08,
127.95, 127.65, 127.07, 125.17, 119.93, 81.89, 66.90,
64.57, 52.38, 47.16, 42.01, 37.39, 33.49, 27.97. MS
(FAB+) 588.2 (MH+). Mp (ꢁC) 90.
Nꢀ-Carbobenzyloxy-L-ornithinylglycine tert-butyl ester
(3f). This compound was prepared using general proce-
dure F to give the product as a light yellow viscous solid
(92% yield). IR nmax (cmꢀ1) 3072 (NH2); 1745, 1723,
1
1675 (C¼O). H NMR(CDCl , 400 MHz) d 7.32–7.28
3
(m, 5H), 6.03 (s, 2H), 5.44 (s, 1H), 5.27 (s, 1H), 5.05 (s,
2H), 3.91 (t, 1H, J=6.8 Hz), 3.83 (s, 2H), 2.99 (t, 2H,
J=4.5 Hz), 1.94–1.36 (m, 13H). 13C NMR(CDCl
,
3
Nꢀ-Carbobenzyloxy-Nꢂ-9-fluorenylmethoxycarbonyl-L-
ornithinylglycine tert-butyl ester (3e). This compound
was prepared using general procedure E to give the
product as a yellow light powder (97% yield). IR nmax
(cmꢀ1) 1754, 1725, 1700, 1660 (C¼O). 1H NMR
(CDCl3, 400 MHz) d 7.74 (d, 2H, J=7.7 Hz), 7.59 (d,
2H, J=7.6 Hz), 7.40–7.32 (m, 9H), 6.43 (s, 1H), 5.43 (s,
1H), 5.09 (s, 2H), 4.93 (s, 1H), 4.45–4.36 (m, 3H), 4.23
(t, 1H, J=6.2 Hz), 3.89 (s, 2H), 3.01 (t, 2H, J=5.4 Hz),
1.71–1.45 (m, 13H). 13C NMR(CDCl 3, 100 MHz) d
172.16, 168.75, 156.97, 156.38, 143.94, 141.25, 136.25,
128.49, 128.12, 128.02, 127.65, 127.03, 125.08, 119.93,
82.14, 66.94, 66.60, 53.50, 47.21, 41.92, 39.81, 30.12, 27,
96, 25.99. MS (FAB+) 602.4 (MH+). Mp (ꢁC) 112.
100 MHz) d 172.59, 168.89, 156.40, 136.43, 128.34,
127.89, 127.82, 81.65, 66.53, 54.46, 41.77, 30.19, 28.86,
27.88, 20.96. MS (FAB+) 380.2 (MH+).
Nꢀ-Carbobenzyloxy-L-lysylglycine tert-butyl ester (4f).
This compound was prepared using general procedure
F to give the product as a light yellow viscous solid
(93% yield). IR nmax (cmꢀ1) 3104 (NH2); 1745, 1727,
1
1671 (C¼O). H NMR(CDCl , 400 MHz) d 7.32–7.29
3
(m, 5H), 6.01 (s, 2H), 5.45 (s, 1H), 5.29 (s, 1H), 5.06 (s,
2H), 3.90 (t, 1H, J=6.6 Hz), 3.82 (s, 2H), 2.97 (t, 2H,
J=3.5 Hz), 1.96–1.37 (m, 15H). 13C NMR(CDCl
,
3
100 MHz) d 172.44, 168.56, 156.09, 136.29, 128.09,
127.63, 127.51, 81.84, 66.19, 54.54, 41.50, 32.11, 31.77,
28.51, 27.61, 22.37. MS (FAB+) 393.3 (MH+).
Nꢀ-Carbobenzyloxy-N"-9-fluorenylmethoxycarbonyl-L-
lysylglycine tert-butyl ester (4e). This compound was
prepared using general procedure E to give the product
as a white powder (97% yield). IR nmax (cmꢀ1) 1750,
1720, 1700, 1658 (C¼O). 1H NMR(CDCl 3, 400 MHz) d
7.76 (d, 2H, J=7.6 Hz), 7.58 (d, 2H, J=7.5 Hz), 7.41–
7.31 (m, 9H), 6.43 (s, 1H), 5.41 (s, 1H), 5.10 (s, 2H), 4.91
(s, 1H), 4.44–4.36 (m, 3H), 4.21 (t, 1H, J=6.1 Hz), 3.92
(s, 2H), 3.08 (t, 2H, J=4.2 Hz), 1.70–1.39 (m, 15H). 13C
NMR(CDCl 3, 100 MHz) d 171.87, 168.67, 156.56,
156.23, 143.91, 141.15, 136.09, 128.39, 128.04, 127.92,
127.53, 126.92, 124.96, 119.83, 82.16, 66.88, 66.37,
54.58, 47.13, 40.17, 31.84, 29.19, 27.90, 22.14. MS
(FAB+) 616.4 (MH+). Mp (ꢁC) 119.
Nꢀ-Carbobenzyloxy-2-amino-Nꢃ-(3-methoxy-5-[1,2,4]thia-
diazolylamino)-L-propionylglycine tert-butyl ester (1g).
This compound was prepared using general procedure
G to give the product as a light orange powder (19%
yield). IR nmax (cmꢀ1) 1745, 1727, 1670 (C¼O). 1H
NMR(CDCl , 400 MHz) d 7.35–7.30 (m, 5H), 6.77 (s,
3
1H), 5.55 (s, 1H), 5.32 (s, 1H), 5.09 (s, 2H), 4.26 (t, 1H,
J=6.8 Hz), 3.95 (s, 3H), 3.80 (s, 2H), 3.24 (t, 2H, J=6.5
Hz), 1.49 (s, 9H). 13C NMR(CDCl 3, 100 MHz) d
183.76, 170.91, 169.23, 168.16, 156.86, 136.47, 128.76,
128.37, 128.20, 82.54, 67.41, 56.35, 53.92, 46.54, 41.40,
27.24. MS (FAB+) 466.2 (MH+). Mp (ꢁC) 82.
Nꢀ-Carbobenzyloxy-2-amino-Nꢃ-(3-methoxy-5-[1,2,4]thia-
diazolylamino)-L-butyrylglycine tert-butyl ester (2g).
This compound was prepared using general procedure
G to give the product as a light orange powder (21%
yield). IR nmax (cmꢀ1) 1749, 1730, 1674 (C¼O). 1H
Nꢀ-Carbobenzyloxy-2,3-diamino-L-propionylglycine tert-
butyl ester (1f). This compound was prepared using
general procedure F to give the product as a light yellow
viscous solid (93% yield). IR nmax (cmꢀ1) 3099 (NH2);
1744, 1724, 1670 (C¼O). 1H NMR(CDCl 3, 400 MHz) d
NMR(CDCl , 400 MHz) d 7.34 (m, 5H), 6.79 (s, 1H),
3