ACS Chemical Neuroscience
Research Article
Ethyl 2-[[(E)-Octadec-11-enoyl]amino]acetate. Yield = 90%, white
powder. Mp = 49−50 °C. 1H NMR (500 MHz, DMSO-d6) δ 8.18 (t, J =
6.0 Hz, 1H), 5.35−5.30 (m, 2H), 4.06 (q, J = 7.0 Hz, 2H), 3.76 (d, J = 6.0
Hz, 2H, 2H), 2.09 (t, J = 7.5 Hz, 2H), 1.98−1.88(m, 4H), 1.47 (p, J = 7.0
Hz, 2H), 1.32−1.20 (m, 20H), 1.17 (t, J = 7.0 Hz, 3H), 0.84 (t, J = 7.0
Hz, 3H). 13C NMR (100 MHz, DMSO-d6): δ 175.81, 173.11, 132.76
(2C), 63.39, 43.73, 38.12, 34.25, 32.24, 32.21, 32.05, 31.97, 31.92, 31.72,
31.67, 31.39, 29.72, 29.70, 28.30, 25.21, 17.18, 17.05. HRMS (ESI) m/z
[M + H]+ calcd for C22H42NO3, 368.3159; found, 368.3158.
Ethyl 2-[[(E)-Octadec-9-enoyl]amino]acetate. Yield = 90%, white
powder. Mp = 62−63 °C. 1H NMR (500 MHz, DMSO-d6) δ 8.18 (t, J =
6.0 Hz, 1H), 5.36−5.34 (m, 2H), 4.06 (q, J = 7.0 Hz, 2H), 3.76 (d, J = 6.0
Hz, 2H, 2H), 2.09 (t, J = 7.5 Hz, 2H), 1.94−1.91 (m, 4H), 1.47 (p, J = 7.0
Hz, 2H), 1.30−1.23 (m, 20H), 1.17 (t, J = 7.0 Hz, 3H), 0.84 (t, J = 7.0
Hz, 3H). 13C NMR (100 MHz, DMSO-d6): δ 172.86, 170.16, 130.23
(2C), 60.44, 40.78, 35.15, 32.11, 31.43, 29.16, 29.15, 28.98 (2C), 28.85,
28.80, 28.65, 28.56 (2C), 25.33, 22.25, 14.23, 14.11. HRMS (ESI) m/z
[M + H]+ calcd for C22H42NO3, 368.3159; found, 368.3155.
2636, 25.51, 22.27, 14.24, 14.13. HRMS (ESI) m/z [M + H]+ calcd for
C20H38NO3, 340.2846; found, 340.2849.
Ethyl 2-[[(Z)-Hexadec-4-enoyl]amino]acetate. Yield = 56%, color-
less liquid. 1H NMR (500 MHz, DMSO-d6) δ 8.23 (t, J = 6.0 Hz, 1H),
5.32−5.30 (m, 2H), 4.06 (q, J = 7.0 Hz, 2H), 3.77 (d, J = 6.0 Hz, 2H),
2.20 (t, J = 7.0 Hz, 2H), 2.15−2.12 (m, 2H), 1.99−1.97 (m, 2H), 1.29−
1.23(m, 16H), 1.17 (t, J = 7.0 Hz, 3H), 0.84 (t, J = 7.0 Hz, 3H). 13C
NMR (100 MHz, DMSO-d6): δ 172.08, 169.93, 130.21, 129.36, 60.29,
40.60, 34.98, 31.28, 29.04, 29.02, 28.99, 28.91, 28.70, 26.64, 26.57, 23.01,
22.08, 20.74, 14.04, 13.93. HRMS (ESI) m/z [M + H]+ calcd for
C20H38NO3, 340.2846; found, 340.2848.
Ethyl 2-[[(Z)-Tetradec-9-enoyl]amino]acetate. Yield = 70%, color-
less liquid. 1H NMR (500 MHz, DMSO-d6): δ 8.19 (t, J = 6.0 Hz, 1H),
5.32−5.30 (m, 2H), 4.07 (q, J = 7.0 Hz, 2H), 3.77 (d, J = 6.0 Hz, 2H),
2.10 (t, J = 7.5 Hz, 2H), 2.05−1.90 (m, 4H), 1.47 (p, J = 7.5 Hz, 2H),
1.30−1.20 (m, 12H), 1.17 (t, J = 7.0 Hz, 2H), 0.85 (t, J = 7.0 Hz, 3H).
13C NMR (100 MHz, DMSO-d6): δ 172.64, 169.97, 129.61, 129.58,
60.26, 40.60, 34.97, 31.35, 29.09, 28.65, 28.52, 28.51, 26.58, 26.30, 25.15,
21.69, 14.04, 13.79. HRMS (ESI) m/z [M + H]+ calcd for C18H34NO3,
312.2533; found, 312.2529.
Ethyl 2-[[(Z)-Hexadec-13-enoyl]amino]acetate. Yield = 87%,
1
colorless liquid. H NMR (500 MHz, CDCl3) δ 5.92 (s, 1H), 5.40−
5.30 (m, 2H), 4.22 (q, J = 7.0 Hz, 2H), 4.02 (d, J = 5.5 Hz, 2H), 2.23 (t, J
= 7.5 Hz, 2H), 2.08−1.95 (m, 4H), 1.64 (p, J = 7.0 Hz, 2H), 1.35−1.20
(m, 19H), 0.96 (t, J = 7.5 Hz, 3H). 13C NMR (100 MHz, CDCl3): δ
173.21, 170.13, 131.45, 129.33, 61.51, 41.33, 36.45, 29.76, 29.58, 29.57,
29.51, 29.44, 29.31, 29.27, 29.24, 27.08, 25.56, 20.48, 14.38, 14.12.
HRMS (ESI) m/z [M + H]+ calcd for C20H38NO3, 340.2846; found,
340.2840.
General Procedure for Synthesis of 3−20. To a solution of the
ethyl ester (0.51 mmol) in ethanol (30 mL) was added 1 M NaOH (10
mL). The solution was stirred at 40 °C for 3 h. The ethanol was removed
under reduced pressure, and the aqueous residue was adjusted to pH 2
with 0.5 M HCl. The resulting suspension was filtered and the solid
product washed with water (10 mL) and ethanol (5 mL).
2-[[(Z)-Octadec-15-enoyl]amino]acetic Acid (3). Yield = 87%, white
powder. Mp = 87−89 °C. 1H NMR (500 MHz, CDCl3) δ 6.02 (s, 1H),
5.40−5.30 (m, 2H), 4.09 (d, J = 5.5 Hz, 2H), 2.27 (t, J = 7.5 Hz, 2H),
2.10−1.95 (m, 4H), 1.65 (p, J = 7.0 Hz, 2H), 1.35−1.20 (m, 20H), 0.96
(t, J = 7.5 Hz, 3H). 13C NMR (100 MHz, DMSO-d6): δ 172.95, 171.86,
131.71, 129.46, 40.97, 35.50, 29.56, 29.46, 29.44, 29.38, 29.32, 29.25,
29.05, 29.04, 26.93, 25.63, 20.46, 14.69. HRMS (ESI) m/z [M + H]+
calcd for C20H38NO3, 340.2846; found, 340.2847. Anal. Calcd for
C20H37NO3·1/4H2O: C 69.83, H 10.99, N 4.07. Found: C 69.95, H
11.17, N 4.03.
2-[[(Z)-Octadec-13-enoyl]amino]acetic Acid (4). Yield = 77%, white
powder. Mp = 95−96 °C. 1H NMR (500 MHz, DMSO-d6): δ 8.06 (t, J =
5.5 Hz, 1H), 5.32−5.30 (m, 2H), 3.70 (d, J = 6.0HZ, 2H), 2.09 (t, J = 7.5
Hz, 2H), 1.98−1.95 (m, 4H), 1.47 (p, J = 7.0 Hz, 2H), 1.31−1.23 (m,
20H), 0.84 (t, J = 7.0 Hz, 3H). 13C NMR (100 MHz, DMSO-d6): δ
172.37, 171.38, 129.63, 129.59, 40.82, 35.09, 31.36, 29.08, 29.00 (2C),
28.94, 28.85, 28.81, 28.62, 28.57, 26.55, 26.30, 25.19, 21.70, 13.81.
HRMS (ESI) m/z [M + H]+ calcd for C20H38NO3, 340.2846; found,
340.2850. Anal. Calcd for C20H37NO3·1/4H2O: C 69.83, H 10.99, N
4.07. Found: C 69.88, H 11.03, N 4.15.
2-[[(Z)-Octadec-12-enoyl]amino]acetic Acid (5). Yield = 78%, white
powder. Mp = 94−95 °C. 1H NMR (500 MHz, DMSO-d6): δ 7.90 (t, J =
5.5 Hz, 1H), 5.32−5.30 (m, 2H), 3.61(d, J = 5.5HZ, 2H), 2.08(t, J = 7.5
Hz, 2H), 1.99−1.95(m, 4H), 1.46 (p, J = 7.0 Hz, 2H), 1.30−1.22 (m,
20H), 0.84 (t, J = 7.0 Hz, 3H) . 13C NMR (100 MHz, DMSO-d6): δ.
172.33, 171.35, 129.62, 129.61, 40.84, 35.08, 30.85, 29.07, 28.92, 28.84
(2C), 28.80, 28.79 (2C), 28.61, 28.56, 26.54, 25.18, 21.95, 13.91. HRMS
(ESI) m/z [M + H]+ calcd for C20H38NO3, 340.2846; found, 340.2850.
Anal. Calcd for C20H37NO3·1/2H2O: C 68.92, H 10.99, N 3.92. Found:
C 68.61, H 11.03, N 3.96.
Ethyl 2-[[(Z)-Hexadec-11-enoyl]amino]acetate. Yield = 66%,
1
colorless liquid. H NMR (500 MHz, DMSO-d6) δ 8.18 (t, J = 6.0
Hz, 1H), 5.33−5.31 (m, 2H), 4.07 (q, J = 7.0 Hz, 2H), 3.76 (d, J = 6.0
Hz, 2H), 2.09 (t, J = 7.5 Hz, 2H), 1.98−1.95 (m, 4H), 1.46 (p, J = 7.0 Hz,
2H), 1.28−1.23 (m, 16H), 1.16 (t, J = 7.0 Hz, 3H), 0.88 (t, J = 7.0 Hz,
3H). 13C NMR (100 MHz, DMSO-d6): δ 172.87, 170.16, 129.80,
129.77, 60.44, 40.78, 35.16, 31.53, 29.28, 29.08, 29.00, 28.95, 28.75,
28.70, 26.74, 26.47, 25.34, 21.88, 14.23, 13.98. HRMS (ESI) m/z [M +
H]+ calcd for C20H38NO3, 340.2846; found, 340.2847.
Ethyl 2-[[(Z)-Hexadec-10-enoyl]amino]acetate. Yield = 71%,
1
colorless liquid. H NMR (500 MHz, DMSO-d6) δ 8.18 (t, J = 6.0
Hz, 1H), 5.35−5.33 (m, 2H), 4.06 (q, J = 7.0 Hz, 2H), 3.76 (d, J = 5.5
Hz, 2H), 2.09 (t, J = 7.5 Hz, 2H), 1.99−1.95 (m, 4H), 1.46 (p, J = 7.0 Hz,
2H), 1.30−1.23 (m, 16H), 1.17(t, J = 7.0 Hz, 3H), 0.84 (t, J = 7.0 Hz,
3H). 13C NMR (100 MHz, DMSO-d6): δ 172.87, 170.16, 129.64,
129.45, 60.44, 40.75, 35.13, 31.50, 29.28, 29.08, 28.99, 28.95, 28.75,
28.70, 26.70, 26.43, 25.34, 21.85, 14.23, 13.98. HRMS (ESI) m/z [M +
H]+ calcd for C20H38NO3, 340.2846; found, 340.2846.
Ethyl 2-[[(Z)-Hexadec-9-enoyl]amino]acetate. Yield = 65%, color-
less liquid. 1H NMR (500 MHz, DMSO-d6) δ 8.15 (t, J = 6.0 Hz, 1H),
5.29−5.27 (m, 2H), 4.05 (q, J = 7.0 Hz, 2H), 3.74 (d, J = 5.5 Hz, 2H),
2.07 (t, J = 7.5 Hz, 2H), 1.96−1.92 (m, 4H), 1.45 (p, J = 7.0 Hz, 2H),
1.27−1.21 (m, 16H), 1.15 (t, J = 7.0 Hz, 3H), 0.82 (t, J = 7.0 Hz, 3H).
13C NMR (100 MHz, DMSO-d6): δ 172.78, 170.12, 129.75, 129.69,
60.41, 40.75, 34.78, 31.43, 29.27, 29.10, 29.00, 28.84, 28.78, 28.37, 26.76,
26.72, 25.21, 22.24, 14.22, 14.11. HRMS (ESI) m/z [M + H]+ calcd for
C20H38NO3, 340.2846; found, 340.2850.
Ethyl 2-[[(Z)-Hexadec-7-enoyl]amino]acetate. Yield = 63%, color-
less liquid. 1H NMR (500 MHz, DMSO-d6) δ 8.18 (t, J = 6.0 Hz, 1H),
5.32−5.30 (m, 2H), 4.06 (q, J = 7.0 Hz, 2H), 3.77 (d, J = 6.0 Hz, 2H),
2.09 (t, J = 7.5 Hz, 2H), 1.97−1.95 (m, 4H), 1.48 (p, J = 7.5 Hz, 2H),
1.30−1.23 (m, 16H), 1.17 (t, J = 7.0 Hz, 3H), 0.84 (t, J = 7.0 Hz, 3H).
13C NMR (100 MHz, DMSO-d6): δ 172.78, 170.12, 129.79, 129.69,
60.41, 40.75, 35.10, 31.43, 29.27, 29.10, 29.00, 28.84, 28.78, 28.37, 26.74,
26.71, 25.21, 22.24, 14.20, 14.08. HRMS (ESI) m/z [M + H]+ calcd for
C20H38NO3, 340.2846; found, 340.2850.
Ethyl 2-[[(Z)-Hexadec-5-enoyl]amino]acetate. Yield = 50%, color-
less liquid. 1H NMR (500 MHz, DMSO-d6) δ 8.20 (t, J = 5.5 Hz, 1H),
5.34−5.30 (m, 2H), 4.06 (q, J = 7.0 Hz, 2H), 3.77 (d, J = 6.0 Hz, 2H),
2.10 (t, J = 7.5 Hz, 2H), 2.00−1.95 (m, 4H), 1.52 (p, J = 7.0 Hz, 2H),
1.28−1.23 (m, 16H), 1.17 (t, J = 7.0 Hz, 3H), 0.84 (t, J = 7.0 Hz, 3H).
13C NMR (100 MHz, DMSO-d6): δ 172.73, 170.19, 130.34, 129.22,
60.45, 40.80, 34.70, 31.47, 29.32, 29.22, 29.10, 29.08, 28.88, 28.83, 26.79,
2-[[(Z)-Octadec-11-enoyl]amino]acetic Acid (6). Yield = 87%, white
powder. Mp = 92−93 °C. 1H NMR (500 MHz, DMSO-d6): δ 8.00 (t, J =
5.5 Hz, 1H), 5.32−5.30 (m, 2H), 3.65 (d, J = 6.0 Hz, 2H), 2.07 (t, J = 7.5
Hz, 2H), 1.99−1.95(m, 4H), 1.46 (p, J = 6.5 Hz, 2H), 1.30−1.22(m,
20H), 0.84 (t, J = 7.0 Hz, 3H). 13C NMR (100 MHz, DMSO-d6): δ
172.53, 171.61, 129.80 (2C), 41.03, 40.20, 35.27, 31.30, 29.28, 29.26,
29.11, 29.04, 28.99, 28.81, 28.77, 28.44, 26.76, 25.37, 22.26, 14.10.
HRMS (ESI) m/z [M + H]+ calcd for C20H38NO3, 340.2846; found,
340.2840. Anal. Calcd for C20H37NO3·1/4H2O: C 69.83, H 10.99, N
4.07. Found: C 69.84, H 11.01, N 3.94.
2-[[(Z)-Octadec-10-enoyl]amino]acetic Acid (7). Yield = 92%, white
powder. Mp = 85−86 °C. 1H NMR (500 MHz, DMSO-d6): δ 8.04 (t, J =
5.5 Hz, 1H), 5.32−5.30 (m, 2H), 3.70 (d, J = 6.0HZ, 2H), 2.08 (t, J = 7.5
Hz, 2H), 1.99−1.95 (m, 4H), 1.47 (p, J = 7.0 Hz, 2H), 1.30−1.23 (m,
H
ACS Chem. Neurosci. XXXX, XXX, XXX−XXX