Acetic Acid → HCID 57512042, compound

Participants

Reaction Steps

To a stirred solution of acetic acid (15 pg, 0.2 mmol), amine 92 (100 mg, 0.2 mmol), and HATU (80 mg, 0.2 mmol) in methylene chloride (3 mL) was added N,N-diisopropylethylamine (130 μL, 0.7 mmol). The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was partitioned between methylene chloride and water. The organic layer was washed with water, dried (sodium sulfate), filtered, and concentrated under reduced pressure to afford a crude oil. Purification by flash column chromatography (silica, gradient 95:5 to 90:10 methylene chloride/methanol) provided N-{(1S,2R)-3-[(3-ethylbenzyl)amino]-1-[3-(hexyloxy)benzyl]-2-hydroxypropyl}acetamide 93B (20 mg): mp 102–105° C.; IR (KBr) 3304, 2929, 1637, 1603, 1550 cm 1; 1H NMR (500 MHz, CD3OD)δ 7.26–7.11 (m, 5H), 6.75–6.70 (m, 3H), 4.03–3.60 (m, 6H), 3.10–3.05 (m, 1H), 2.80–2.55 (m, 5H), 1.78–1.72 (m, 2H), 1.78 (s, 3H), 1.46–1.44 (m, 2H), 1.36–1.33 (m, 4H), 1.24–1.21 (m, 3H), 0.93–0.91 (m, 3H); ESI MS m/z 441 [M+H]+.

Provenance & Evidence