SYNTHESIS OF 3,4-DISUBSTITUTED 4-AMINOBUTANOIC ACIDS
905
+
13
under reduced pressure (15–20 mm), and the precip-
itate was filtered off. Yield 0.59 g (40%), decomposi-
tion point 208–210°C (from MeOH); published data:
mp 197°C [3], 198–200°C [4], 205–207°C [5]. IR
7.70 m (4H, C H ), 8.54 s (3H, NH ). C NMR spec-
6
4
3
2
3
trum, δ , ppm: 30.70 (C ), 31.75 (CH ), 33.04 (C ),
64.52 (C ); 112.67, 114.82, 125.82, 126.12, 127.08,
128.82, 128.90, 135.62, 151.75 (Carom); 168.42 (C ).
Found, %: C 62.30, 62.31; H 5.57, 5.58; N 12.34,
12.25. C H ClN O . Calculated, %: C 62.52; H 5.83;
C
3
4
1
–
1
+
spectrum, ν, cm : 3650–2500 (NH ), 1717 (C=O).
3
1
2
H NMR spectrum, δ, ppm: 2.19 d.d (1H, 2-H, J =
6.0, J = 4.1 Hz), 2.41 d.d (1H, 2-H, J = 16.0, J =
1.0 Hz), 3.64 m (1H, 3-H), 4.42 d (1H, 4-H, J =
1
8
20
3
2
3
2
3
1
1
N 12.15.
3
The spectral data and elemental analyses were
obtained using the facilities of the Joint Center, Faculty
of Chemistry, Herzen State Pedagogical University of
Russia. The H NMR and H– C HMQC spectra were
recorded on a Jeol ECX400A spectrometer at 399.78
8
.8 Hz), 7.20–7.40 m and 7.49 m (5H, C H ), 8.45 s
6
5
+
13
2
(
3H, NH ). C NMR spectrum, δ , ppm: 37.61 (C ),
3 C
3
4
4
1
6.39 (C ), 59.14 (C ); 128.02, 128.52, 129.10, 129.27,
1
1
13
1
36.98, 139.41 (C H ); 172.46 (C ).
6
5
1
13
Compounds 6–8 were synthesized in a similar way.
-Amino-3-(4-aminophenyl)-4-phenylbutanoic
acid dihydrochloride (6). Yield 40%, decomposition
( H) and 100.525 MHz ( C) using DMSO-d as
6
solvent and internal standard. The IR spectra were
measured in KBr on a Shimadzu IR Prestige-21 spec-
trometer with Fourier transform. The elemental com-
positions were determined using a EuroVector EA
3000 analyzer (CHN Dual mode). The melting points
were determined on a PTP (M) melting point
apparatus.
4
–
1
point 117–120°C (from MeOH). IR spectrum, ν, cm :
+
1
3
450–2400 (NH ), 1725 (C=O). H NMR spectrum, δ,
3
2
3
ppm: 2.76 d.d (1H, 2-H, J = 17.0, J = 8.8 Hz),
.08 d.d (1H, 2-H, J = 17.0, J = 12.5 Hz), 4.28 m
1H, 3-H), 5.00 d (1H, 4-H, J = 8.0 Hz), 7.05 m (5H,
C H ), 6.83–7.35 m (4H, C H ), 8.43 s (3H, 4-NH ),
.68 s (3H, 4′-NH ). C NMR spectrum, δ , ppm:
7.12 (C ), 44.76 (C ), 60.15 (C ); 127.47, 128.50,
28.57, 129.85, 136.22, 139.40 (Carom); 172.45 (C ).
2
3
3
(
3
+
3
6
5
6
4
This study was performed under financial support
by the Ministry of Education and Science of the
Russian Federation in the framework of the base part
of state assignment.
+
13
8
3
1
3
C
2
3
4
1
Found, %: C 55.90; H 5.85; N 8.13. C H Cl N O .
1
6
20
2
2
2
Calculated, %: C 55.99; H 5.87; N 8.16.
-Amino-3-(pyridin-3-yl)-4-phenylbutanoic acid
hydrochloride (7). Yield 40%, decomposition point
REFERENCES
4
1
. Lapin, I., CNS Drug Rev., 2001, vol. 7, p. 471.
–
1
2
3
13–215°C (from MeOH). IR spectrum, ν, cm :
2. Mashkovskii, M.D., Lekarstvennye sredstva (Medicines),
+
1
Moscow: Novaya Volna, 2012, 16th ed., pp. 49, 121.
450–2350 (NH ), 1720 (C=O). H NMR spectrum, δ,
3
2
3
ppm: 2.06 d.d (1H, 2-H, J = 16.9, J = 3.5 Hz),
2
3. Vasil’eva, O.S., Grineva, V.S., Zobacheva, M.M.,
Kiseleva, I.N., Smirnova, A.A., and Shalyuta, A.D.,
Abstracts of Papers, XXVI Gertsenovskie chteniya.
Khimiya (XXVIth Herzen Readings. Chemistry), 1973,
vol. 2, p. 25.
2
3
.79 d.d (1H, 2-H, J = 16.9, J = 11.9 Hz), 4.02 m
3
(
(
1H, 3-H), 4.71 d (1H, 4-H, J = 8.5 Hz), 7.45–7.75 m
5H, C H ), 8.07–9.21 m (4H, pyridine), 8.82 s (3H,
6
13
5
+
3
2
NH ). C NMR spectrum, δ , ppm: 37.46 (C ), 43.70
C
3
4
4. Potapov, V.M., Gracheva, R.A., Sivov, N.A., Savi-
na, S.A., and Sivova, L.A., J. Org. Chem. USSR, 1989,
vol. 25, p. 1694.
(
C ), 58.19 (C ); 127.60, 128.66, 129.60, 129.72,
1
1
36.98, 140.11, 141.28, 142.94, 147.04 (C H , Py),
72.04 (C ). Found, %: C 61.45, 61.48; H 5.79, 5.83;
6 5
1
5
. Dryanska, V. and Pashkuleva, I., Org. Prep. Proced. Int.,
999, vol. 31, p. 232.
N 9.70, 9.79. C H ClN O . Calculated, %: C 61.54;
1
5
17
2
2
1
H 5.85; N 9.75.
6
. Berestovitskaya, V.M., Zobacheva, M.M., and Vasil’e-
va, O.S., Izv. Ross. Gos. Ped. Univ. imeni A.I. Gertsena.
Estestv. Tochn. Nauki, 2002, vol. 2, no. 4, p. 133.
4
-Amino-3-(1-methyl-1H-benzimidazol-2-yl)-4-
phenylbutanoic acid hydrochloride (8). Yield 55%,
decomposition point 265–267°C (from MeOH). IR
7
8
. Berestovitskaya, V.M., Vasil’eva, O.S., and Ostroglya-
dov, E.S., 2-Pirrolidon i ego proizvodnye (Pyrrolidin-2-
one and Its Derivatives), St. Petersburg: Asterion, 2013.
–
1
+
spectrum, ν, cm : 3500–2400 (NH ), 1710 (C=O).
3
1
2
H NMR spectrum, δ, ppm: 2.85 d.d (1H, 2-H, J =
6.9, J = 9.8 Hz), 3.50 d.d (1H, 2-H, J = 16.9, J =
.5 Hz), 3.88 s (3H, CH ), 4.90 m (1H, 3-H), 5.40 d
1H, 4-H, J = 8.5 Hz), 7.07 m (5H, C H ), 7.40–
3
2
3
1
7
(
. Nikonorov, A.A., Ostroglyadov, E.S., Vasil’eva, O.S., and
Berestovitskaya, V.M., Russ. J. Gen. Chem., 2010,
vol. 80, p. 2396.
3
3
6
5
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 52 No. 6 2016