Diisopropylethylamine → HCID 57512640, compound

Participants

Reaction Steps

To a stirred solution of 2-[(methylsulfonyl)amino]-1,3-oxazole-4-carboxylic acid (43) (100 mg, 0.5 mmol) and HATU (180 mg, 0.5 mmol) in methylene chloride (3 mL) was added N,N-diisopropylethylamine (100 μL, 0.6 mmol). In a separate flask, N,N-diisopropylethylamine (200 μL, 1.2 mmol) was added to amine 48 (135 mg, 0.3 mmol) in methylene chloride (2 mL). This solution was added to the above solution containing the acid and the resulting 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 93:7 to 90:10 methylene chloride/methanol) provided N-{(1S,2R)-1-(3-butoxybenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-2-[(methylsulfonyl)amino]-1,3-oxazole-4-carboxamide (50a) (10 mg): mp 78–80° C.; IR (KBr) 2960, 1602, 1581, 1490, 1450 cm−1; 1H NMR (500 MHz, CD3OD) δ 7.67 (s, 1H), 7.34–7.09 (m, 5H), 6.82–6.68 (m, 3H), 4.18 (s, 2H), 4.07–4.05 (m, 1H), 3.90–3.84 (m, 3H), 3.23–3.16 (m, 2H), 3.04 (s, 3H), 3.04–3.01 (m, 1H), 2.75–2.64 (m, 3H), 1.69–1.66 (m, 2H), 1.46–1.42 (m, 2H), 1.21 (t, J=8 Hz, 3H), 0.94 (t, J=8 Hz, 3H); ESI-MS m/z 559 [M+H]+.

Provenance & Evidence