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4.2.12. Octadecyl 3,4,5-trihydroxybenzoate (6d)
4.2.20. Dodecyl 3,4,5-trihydroxybenzamide (8c)
According to the same procedure used for 6a, starting from 5d
(388 mg, 0.560 mmol), 6d (230 mg, 0.544 mmol, 97%) was ob-
tained. 1H NMR (500 MHz, DMSO-d6) d 9.24 (s, 2H), 8.92 (s, 1H),
6.92 (s, 2H), 4.13 (t, J = 6.5 Hz, 2H), 1.63 (quint, J = 6.5 Hz, 2H),
1.38-1.16 (m, 30H), 0.84 (t, J = 6.5 Hz, 3H).
According to the same procedure used for 6a, starting from 7c
(248 mg, 0.408 mmol), 8d (100 mg, 0.296 mmol, 73%) was ob-
tained. 1H NMR (500 MHz, DMSO-d6) d 8.97 (s, 2H), 8.60 (s, 1H),
8.00 (t, J = 6.5 Hz, 1H), 6.78 (s, 2H), 3.13 (q, J = 6.5 Hz, 2H), 1.45–
1.42 (m, 2H), 1.28-1.18 (m, 18H), 0.84 (t, J = 6.5 Hz, 3H).
4.2.13. Ethyl 3,4,5-tribenzyloxybenzamide (7a)
4.2.21. Octadecyl 3,4,5-trihydroxybenzamide (8d)
According to the same procedure used for 6a, starting from
7d (284 mg, 0.410 mmol), 8d (166 mg, 0.394 mmol, 96%) was
obtained. 1H NMR (500 MHz, DMSO-d6) d 8.97 (s, 2H), 8.59 (s,
1H), 8.00 (t, J = 6.5 Hz, 1H), 6.78 (s, 2H), 3.13 (q, J = 6.5 Hz,
2H), 1.45–1.42 (m, 2H), 1.27–1.18 (m, 30H), 0.84 (t, J = 6.5 Hz,
3H).
To a stirred solution of 4 (196 mg, 0.445 mmol), EDCI (137 mg,
0.715 mmol) and DMAP (14 mg, 0.115 mmol) in CH2Cl2 (10 mL)
was added ethylamine (78 mg, 1.32 mmol). The reaction mixture
was stirred at room temperature under an N2 atmosphere for 1 h,
washed with water and brine, dried over MgSO4, filtered, and con-
centrated in vacuo. The residue was purified by column chroma-
tography on silica gel (hexane/ethyl acetate = 2:3) to afford 7a
(73 mg, 0.156 mmol, 35%). 1H NMR (500 MHz, CDCl3) d 7.41–7.25
(m, 15H), 7.03 (s, 2H), 5.88 (br, 1H), 5.12 (s, 4H), 5.07 (s, 2H),
3.44 (quint, J = 6.5 Hz, 2H), 1.21 (t, J = 6.5 Hz, 3H). MS (FAB, MH+)
m/z 468.
4.2.22. Docosyl 3,4,5-trihydroxybenzamide (8e)
According to the same procedure used for 6a but with THF as a
solvent instead of AcOEt, starting from 7e (527 mg, 0.704 mmol),
7e (331 mg, 0.693 mmol, 98%) was obtained. 1H NMR (500 MHz,
DMSO-d6) d 8.95 (s, 2H), 8.58 (s, 1H), 7.99 (t, J = 6.5 Hz, 1H), 6.78
(s, 2H), 3.13 (q, J = 6.5 Hz, 2H), 1.47–1.41 (m, 2H), 1.27–1.18 (m,
38H), 0.84 (t, J = 6.5 Hz, 3H).
4.2.14. Hexyl 3,4,5-tribenzyloxybenzamide (7b)
According to the same procedure used for 7a, starting from 4
(187 mg, 0.425 mmol), 7b (189 mg, 0.361 mmol, 85%) was ob-
tained. 1H NMR (500 MHz, DMSO-d6) d 7.41–7.25 (m, 15H), 7.02
(s, 2H), 5.85 (br, 1H), 5.12 (s, 4H), 5.07 (s, 2H), 3.37 (q, J = 6.4 Hz,
2H), 1.54 (br, 2H), 1.42–1.26 (m, 6H), 0.89 (t, J = 6.4 Hz, 3H). MS
(FAB, MH+) m/z 524.
4.2.23. Benzoic acid dodecyl ester (9a)
1H NMR (500 MHz, CDCl3) d 7.94 (d, J = 7.9 Hz, 2H), 7.66–7.63
(br, 1H), 7.52 (t, J = 7.9 Hz, 2H), 4.25 (t, J = 6.7 Hz, 2H), 1.69 (quint,
J = 6.7 Hz, 2H), 1.38 (quint, J = 6.7 Hz, 2H), 1.30–1.22 (m, 16H), 0.83
(t, J = 6.7 Hz, 3H). MS (FAB, MH+) m/z 229.
4.2.15. Dodecyl 3,4,5-tribenzyloxybenzamide (7c)
According to the same procedure used for 7a, starting from 4
(203 mg, 0.461 mmol), 7c (252 mg, 0.415 mmol, 90%) was ob-
tained. 1H NMR (500 MHz, CDCl3) d 7.41–7.25 (m, 15H), 7.02 (s,
2H), 5.84 (t, J = 6.5Hz, 1H), 5.12 (s, 4H), 5.07 (s, 2H), 3.37 (q,
J = 6.5 Hz, 2H), 1.31–1.24 (m, 20H), 0.86 (t, J = 6.5 Hz, 3H). MS
(FAB, MH+) m/z 608.
4.2.24. 3-Hydroxybenzoic acid dodecyl ester (9b)
1H NMR (500 MHz, DMSO-d6) d 9.79 (s, 1H) 7.38–7.28 (m, 3H),
7.01 (d, J = 7.9 Hz, 1H), 4.22 (t, J = 6.7 Hz, 2H), 1.67 (quint,
J = 6.7 Hz, 2H), 1.37 (quint, J = 6.7 Hz, 2H), 1.29–1.22 (m, 16H),
0.84 (t, J = 6.7 Hz, 3H). MS (FAB, MH+) m/z 307.
4.2.25. 4-Hydroxybenzoic acid dodecyl ester (9c)
4.2.16. Octadecyl 3,4,5-tribenzyloxybenzamide (7d)
According to the same procedure used for 7a, starting from 4
(201 mg, 0.456 mmol), 7d (287 mg, 0.415 mmol, 91%) was ob-
tained. 1H NMR (500 MHz, CDCl3) d 7.41–7.25 (m, 15H), 7.02 (s,
2H), 5.84 (t, J = 6.5 Hz, 1H), 5.12 (s, 4H), 5.07 (s, 2H), 3.38 (q,
J = 6.5 Hz, 2H), 1.34–1.21 (m, 30H), 0.86 (t, J = 6.5 Hz, 3H). MS
(FAB, MH+) m/z 692.
1H NMR (500 MHz, CDCl3) d 10.30 (s, 1H), 7.79 (d, J = 1.2, 7.3 Hz,
2H), 6.83 (dd, J = 1.2, 7.3 Hz, 2H), 4,18 (t, J = 6.7 Hz, 2H), 1.65 (quint,
J = 6.7 Hz, 2H) 1.36 (quint, J = 6.7 Hz, 2H) 1.33–1.22 (m, 16H), 0.84
(t, J = 6.7 Hz, 3H). MS (FAB, MH+) m/z 307.
4.2.26. 2,4-Dihydroxybenzoic acid dodecyl ester (9d)
1H NMR (500 MHz, CDCl3) d 11.04 (s, 1H), 7.72 (d, J = 9.2 Hz,
1H), 6.38–6.34 (m, 2H), 5.35 (s, 1H), 4.28 (t, J = 6.7 Hz, 2H), 1.74
(quint, J = 6.7 Hz, 2H) 1.41 (quint, J = 6.7 Hz, 2H), 1.31 (quint,
J = 6.7 Hz, 2H), 1.28–1.24 (m, 14H), 0.86 (t, J = 6.7 Hz, 3H).
4.2.17. Docosyl 3,4,5-tribenzyloxybenzamide (7e)
According to the same procedure used for 7a but with THF as a
solvent instead of CH2Cl2, starting from 4 (357 mg, 0.810 mmol), 7e
(547 mg, 0.731 mmol, 90%) was obtained. 1H NMR (500 MHz,
CDCl3) d 7.42–7.25 (m, 15H), 7.02 (s, 2H), 5.84 (t, J = 6.5 Hz, 1H),
5.12 (s, 4H), 5.07 (s, 2H), 3.38 (q, J = 6.5 Hz, 2H), 1.34-1.21 (m,
40H), 0.86 (t, J = 6.5 Hz, 3H).
4.2.27. 2,3-Dihydroxybenzoic acid dodecyl ester (9e)
1H NMR (500 MHz, CDCl3) d 10.98 (s, 1H), 7.36 (d, J = 7.9 Hz,
1H), 7.08 (d, J = 7.9 Hz, 1H), 6.78 (t, J = 7.9 Hz, 1H), 5.61 (s, 1H)
4.32 (t, J = 6.7 Hz, 2H), 1.76 (quint, J = 6.7 Hz, 2H), 1.41 (quint,
J = 6.7 Hz, 2H), 1.32 (quint, J = 6.7 Hz, 2H), 1.28–1.24 (m, 14H),
0.86 (t, J = 6.7 Hz, 3H). MS (FAB, MH+) m/z 323.
4.2.18. Ethyl 3,4,5-trihydroxybenzamide (8a)
According to the same procedure used for 6a, starting from 7a
(71 mg, 0.152 mmol), 8a (29 mg, 0.147 mmol, 98%) was obtained.
1H NMR (500 MHz, DMSO-d6) d 8.96 (s, 2H), 8.58 (s, 1H), 8.01 (t,
J = 6.4 Hz, 1H), 6.79 (s, 2H), 3.18 (quint, J = 6.4 Hz, 2H), 1.05 (t,
J = 6.4 Hz, 3H).
4.2.28. 3,4-Dihydroxybenzoic acid dodecyl ester (9f)
1H NMR (500 MHz, DMSO-d6) d 9.75 (s, 1H), 9.33 (s, 1H), 7.34–
7.30 (m, 2H), 6.79 (s, 1H), 4.16 (m, 2H), 1.65 (m, 2H), 1.24–1.19 (m,
23H). MS (FAB, MH+) m/z 323.
4.2.19. Hexyl 3,4,5-trihydroxybenzamide (8b)
4.2.29. 3,4,5-Tribenzyloxybenzoyl chloride (10)
According to the same procedure used for 6a, starting from
7b (184 mg, 0.351 mmol), 8b (85 mg, 0.336 mmol, 96%) was
obtained. 1H NMR (500 MHz, DMSO-d6) d 8.97 (s, 2H), 8.59
(s, 1H), 8.00 (t, J = 6.4 Hz, 1H), 6.78 (s, 2H), 3.14 (q,
J = 6.4 Hz, 2H), 1.44 (quint, J = 6.4 Hz, 2H), 1.30-1.20 (m, H),
0.85 (t, J = 6.4 Hz, 3H).
To a stirred solution of 4 (18.0 g, 40.8 mmol) and DMF (0.4 mL)
in toluene (200 mL), oxalyl chloride (7.40 g, 58.3 mmol) was added
slowly. The reaction mixture was stirred at room temperature un-
der an Ar atmosphere, then concentrated in vacuo. The residue was
taken up in 70 volumes of toluene and the solution was filtered.
Cyclohexane (70 mL) was added, and the mixture was cooled to