2300 J . Org. Chem., Vol. 64, No. 7, 1999
Akazome et al.
In clu sion com p ou n d of (R)-(1-n a p h t h yl)glycyl-(R)-
p h en ylglycin e‚eth yl la cta te [(R,R)-1‚2b] com p lex: 75%
yield based on dipeptide; colorless solid; dec 141.5-143 °C
(sintering); 1H NMR (D2O, 300 MHz) δ 8.14-8.05 (m, 3H),
7.75-7.59 (m, 4H), 7.42-7.30 (d like, 5H), 5.98 (s, 1H), 5.18
(s, 1H), 4.37 (q, J ) 7.01 Hz, 1.00H), 4.20 (q, J ) 7.14 Hz,
2.00H), 1.39 (d, J ) 7.01 Hz, 3.00H), 1.11 (t, J ) 7.14 Hz,
dec 109.5-110.5 °C; 1H NMR (D2O, 300 MHz) δ 8.14-8.05 (m,
3H), 7.75-7.59 (m, 4H), 7.42-7.27 (m, 7.50H), 5.96 (s, 1H),
5.35 (s, 0.50H), 5.17 (s, 1H), 3.71 (s, 1.50H); IR (KBr) 3255,
1743, 1671, 1597 cm-1. Anal. Calcd for C20H18N2O3‚0.50C9H10O3‚
1.00H2O: C, 67.57; H, 5.79; N, 6.43. Found: C, 67.47; H, 5.96;
N, 6.18.
In clu sion com p ou n d of (R)-(1-n a p h t h yl)glycyl-(R)-
ph en ylglycin e‚m eth yl 2-h ydr oxy-3-m eth ylbu tyr ate‚m eth -
an ol‚H2O [(R,R)-1‚2k‚MeOH‚H2O] com plex: 81% yield based
3.00H); IR (KBr) 3269, 3219, 1741, 1722, 1671, 1595 cm-1
.
Anal. Calcd for C20H18N2O3 ‚1.00C5H10O3: C, 66.36; H, 6.24;
N, 6.19. Found: C, 66.22; H, 6.23; N, 6.32.
1
on dipeptide; colorless solid; dec 126-127 °C; H NMR (D2O,
In clu sion com p ou n d of (R)-(1-n a p h t h yl)glycyl-(R)-
p h en ylglycin e‚m eth yl 2-h yd r oxybu tyr a te‚H2O [(R,R)-1‚
2e‚H2O] com p lex: 75% yield based on dipeptide; colorless
solid; dec 142-143 °C (sintering); 1H NMR (D2O, 300 MHz) δ
8.14-8.05 (m, 3H), 7.75-7.60 (m, 4H), 7.42-7.30 (d like, 5H),
5.97 (s, 1H), 5.17 (s, 1H), 4.27 (t like, 1.00H), 3.75 (s, 3.00H),
1.87-1.63 (m, 2.00H), 0.91 (t, J ) 7.14 Hz, 3.00H); IR (KBr)
3275, 3222, 1751, 1726, 1670, 1592 cm-1. Anal. Calcd for
300 MHz) δ 8.15-8.07 (m, 3H), 7.77-7.62 (m, 4H), 7.44-7.33
(d like, 5H), 5.98 (s, 1H), 5.19 (s, 1H), 4.16 (d, J ) 4.53 Hz,
0.50H), 3.78 (s, 1.50H), 3.38 (s, 3.00H), 2.13-2.04 (m, 0.50H),
0.97 (d, J ) 6.87 Hz, 1.50H), 0.88 (d, J ) 6.87 Hz, 1.50H); IR
(KBr) 3297, 1725, 1655, 1604 cm-1. Anal. Calcd for C20H18N2O3‚
0.50C6H12O3‚1.00CH4O‚0.50H2O: C, 65.29; H, 6.62; N, 6.35.
Found: C, 65.56; H, 6.43; N, 6.37.
In clu sion com p ou n d of (R)-(1-n a p h t h yl)glycyl-(R)-
p h en ylglycin e‚(S)-m eth yl 2-h yd r oxy-3-m eth ylbu tyr a te
[(R,R)-1‚(S)-2k ] com p lex: 38% yield based on dipeptide;
colorless solid; dec 139.5-140.5 °C (sintering); 1H NMR (D2O,
300 MHz) δ 8.15-8.07 (m, 3H), 7.77-7.62 (m, 4H), 7.44-7.33
(d like, 5H), 5.98 (s, 1H), 5.19 (s, 1H), 4.16 (d, J ) 4.53 Hz,
1.01H), 3.78 (s, 3.03H), 2.13-2.04 (m, 1.01H), 0.97 (d, J ) 6.87
Hz, 3.03H), 0.88 (d, J ) 6.87 Hz, 3.03H); IR (KBr) 3262, 3222,
1751, 1724, 1669, 1591 cm-1. Anal. Calcd for C20H18N2O3‚
1.01C6H12O3: C, 66.90; H, 6.49; N, 5.99. Found: C, 66.63; H,
6.26; N, 6.21.
In clu sion com p ou n d of (R)-(1-n a p h t h yl)glycyl-(R)-
p h en ylglycin e‚m eth yl 3,3-d im eth yl-2-h yd r oxybu tyr a te‚
m eth a n ol‚H2O [(R,R)-1‚2l‚MeOH‚H2O] com p lex: 83% yield
based on dipeptide; colorless unstable solid; 1H NMR (D2O,
300 MHz) δ 8.14-8.05 (m, 3H), 7.76-7.61 (m, 4H), 7.42-7.33
(d like, 5H), 5.96 (s, 1H), 5.18 (s, 1H), 3.97 (s, 0.50H), 3.76 (s,
1.50H), 3.34 (s, 2.10H), 0.94 (s, 4.50H); IR (KBr) 3286, 1719,
1658, 1619 cm-1. Anal. Calcd for C20H18N2O3‚0.50C7H14O3‚
0.70CH4O‚0.50H2O: C, 66.22; H, 6.61; N, 6.38. Found: C,
66.33; H, 6.60; N, 6.53.
X-r a y Cr ysta llogr a p h y. Data collection was performed on
a Mac Science MXC18 four-circle diffractometer with graphite-
monochromated Cu KR (λ ) 1.541 78 Å) radiation using the
2θ-ω scan technique, and the X-ray intensities were measured
up to 2θ ) 140° at 298 or 173 K, respectively. The structures
were solved and refined by a computer program package;
CRYSTAN-GM ver. 6.2.1 or maXus ver. 1.1 from MAC Science
Co. Ltd. The structures solved by a direct method (SIR 9215
on a computer program package).
C
20H18N2O3‚1.00C5H10O3‚0.28H2O: C, 65.62; H, 6.29; N, 6.12.
Found: C, 65.61; H, 6.17; N, 6.24.
In clu sion com p ou n d of (R)-(1-n a p h t h yl)glycyl-(R)-
p h en ylglycin e‚p a n t ola ct on e‚m et h a n ol‚H 2O [(R,R)-1‚2f‚
MeOH‚H2O] com p lex: 82% yield based on dipeptide; colorless
unstable solid; 1H NMR (D2O, 300 MHz) δ 8.15-8.05 (m, 3H),
7.78-7.62 (m, 4H), 7.43-7.32 (d like, 5H), 5.98 (s, 1H), 5.19
(s, 1H), 4.37 (s, 0.50H), 4.11 (ABq, J ) 8.99 Hz, 1.00H), 3.35
(s, 3.00H), 1.18 (s, 1.50H), 1.01 (s, 1.50H); IR (KBr) 3371, 3253,
1774, 1668, 1600 cm-1. Anal. Calcd for C20H18N2O3‚0.50C6H10O3‚
1.00CH4O‚0.36H2O: C, 65.82; H, 6.38; N, 6.40. Found: C,
65.84; H, 6.35; N, 6.32.
In clu sion com p ou n d of (R)-(1-n a p h t h yl)glycyl-(R)-
ph en ylglycin e‚m eth yl 2-h ydr oxyvaler ate‚m eth an ol [(R,R)-
1‚2g‚MeOH] com p lex: 77% yield based on dipeptide; colorless
1
solid; dec 120-122 °C; H NMR (D2O, 300 MHz) δ 8.15-8.05
(m, 3H), 7.78-7.62 (m, 4H), 7.43-7.32 (d like, 5H), 5.98 (s,
1H), 5.19 (s, 1H), 4.40-4.30 (t like, 0.53H), 3.75 (s, 1.59H),
3.34 (s, 3.27H), 1.83-1.60 (m, 1.06H), 1.44-1.25 (m, 1.06H),
0.91 (t, J ) 7.4 Hz, 1.59H); IR (KBr) 3246, 1741, 1670, 1595
cm-1. Anal. Calcd for C20H18N2O3‚0.53C6H12O3‚1.09CH4O: C,
66.35; H, 6.59; N, 6.38. Found: C, 66.04; H, 6.42; N, 6.67.
In clu sion com p ou n d of (R)-(1-n a p h t h yl)glycyl-(R)-
p h en ylglycin e‚m et h yl 2-h yd r oxyh exa n oa t e‚m et h a n ol
[(R,R)-1‚2h ‚MeOH] com p lex: 67% yield based on dipeptide;
colorless solid; dec 98-99 °C; 1H NMR (D2O, 300 MHz) δ 8.15-
8.05 (m, 3H), 7.78-7.62 (m, 4H), 7.43-7.32 (d like, 5H), 5.98
(s, 1H), 5.19 (s, 1H), 4.40-4.30 (t like, 0.50H), 3.75 (s, 1.50H),
3.34 (s, 3.15H), 1.83-1.60 (m, 1.00H), 1.42-1.22 (m, 2.00H),
0.91 (t, J ) 7.1 Hz, 1.50H); IR (KBr) 3242, 1741, 1670, 1584
cm-1. Anal. Calcd for C20H18N2O3‚0.50C7H14O3‚1.05CH4O: C,
66.85; H, 6.67; N, 6.35. Found: C, 66.55; H, 6.39; N, 6.54.
In clu sion com p ou n d of (R)-(1-n a p h t h yl)glycyl-(R)-
ph en ylglycin e‚m eth yl 2-h ydr oxy-4-m eth ylvaler ate‚m eth -
a n ol [(R,R)-1‚2i‚MeOH] com p lex: 80% yield based on
dipeptide; colorless solid; dec 95-96.5 °C; 1H NMR (D2O, 300
MHz) δ 8.15-8.05 (m, 3H), 7.78-7.62 (m, 4H), 7.43-7.32 (d
like, 5H), 5.98 (s, 1H), 5.19 (s, 1H), 4.50-4.37 (t like, 0.52H),
3.75 (s, 1.56H), 3.34 (s, 3.30H), 1.83-1.60 (m, 0.52H), 1.63-
1.53 (m, 1.04H), 0.92 (d, J ) 6.5 Hz, 3.12H); IR (KBr) 3349,
3255, 1735, 1671, 1584 cm-1. Anal. Calcd for C20H18N2O3‚
0.52C7H14O3‚1.10CH4O: C, 66.68; H, 6.71; N, 6.29. Found: C,
66.39; H, 6.59; N, 6.50.
Ack n ow led gm en t. This work was supported by
“Research for the Future” Program (J SPS-RFTF96-
P00304) from The J apan Society for the Promotion of
Science.
Su p p or tin g In for m a tion Ava ila ble: Tables of atomic
coordinates and thermal parameters, bond lengths and angles,
and ORTEP views of inclusion compounds of (S)-2a , (S)-2b,
(S)-2f, (S)-2g, (S)-2h , (S)-2i, (S)-2j, racemic 2k , (S)-2k , and
(S)-2l. This material is available free of charge via the Internet
at http://pubs.acs.org.
J O9818778
In clu sion com p ou n d of (R)-(1-n a p h t h yl)glycyl-(R)-
p h en ylglycin e‚(S)-m eth yl m a n d ela te‚H2O [(R,R)-1‚(S)-2j‚
H2O] com p lex: 47% yield based on dipeptide; colorless solid;
(15) Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.;
Burla, M. C.; Polidori, G.; Camalli, M. J . Appl. Crystallogr. 1994, 27,
435.