Acetic Acid → Eicosa-5,8,11,14-tetraenoic acid (4-chloro-benzyl)-(2,4-dichloro-phenyl)amide

Participants

Reaction Steps

Used the same procedure as above to synthesize 1.15 g (56%) of the desired amine from 4-chlorobenzaldehyde (1.0 g, 7.11 mmol), 2,4-dichloroaniline (1.27 g, 7.83 mmol), sodium triacetoxyborohydride (2.41 g, 11.38 mmol), acetic acid (0.41 mL, 7.11 mmol) and 1,2-dichloroethane (32 mL). 1H NMR δ4.36 (d, 2H, 5.8 Hz), 4.73 (br.s, 1H), 6.46 (d, 1H, 8.5 Hz), 7.03 (dd, 1H, 8.7, 2.2 Hz), 7.22-7.34 (m, 5H). Used the same procedure as above for generating the acid chloride and the subsequent condensation product: used arachidonic acid (234 mg, 0.77 mmol) in CH2Cl2 (5 mL) with oxalyl chloride (147 μL, 1.69 mmol) and DMF (2 drops). The acid chloride in CH2Cl2 (3 mL) was subsequently added to the respective amine (1.1 g, 3.84 mmol) in CH2Cl2 (5 mL). Isolated the desired product (O-2248; 400 mg, 91%) after purification by column chromatography (hexanes/EtOAc 97%/3% then 95%/5%) as a single rotomer. 1H NMR δ0.88 (t, 3H, 6.9 Hz), 1.24-1.41 (m, 6H), 1.67 (q, 2H, 7.1 Hz), 1.94 -2.05 (m, 6H), 2.75 (m, 6H), 4.03 (d, 1H, 14.3 Hz), 5.22-5.40 (m, 8H), 5.48 (d, 1H, 14.3 Hz), 6.70 (d, 1H, 8.5 Hz), 7.10-7.28 (m, 5H), 7.52 (d, 1H, 2.2 Hz). Anal. Calcd for C33H40NOCl3: C, 69.33; H, 7.06. Found: C, 69.17; H, 7.20.

Provenance & Evidence