Diisopropylethylamine → HCID 58746487, compound

Participants

Reaction Steps

(2S)-2-[(tert-Butoxycarbonyl)amino]-3-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)-3-fluorophenyl]propanoic acid (16.7 mg, 0.0400 mmol) in DMF (2.00 mL) was treated with benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (19.5 mg, 0.044 mmol). After five minutes N,N-diisopropylethylamine (20.9 μL, 0.120 mmol) and methyl 2-[(5-aminopentyl)oxy]-6-hydroxybenzoate hydrochloride (14.5 mg, 0.050 mmol) were added and the solution stirred at rt for 1 h. The product was directly purified by preparative LCMS to afford product as a white solid (17.8 mg, 68%). 1H NMR (400 MHz, CD3OD): δ 7.45–7.42 (m, 1H), 7.24–7.21 (m, 1H), 7.16–7.10 (m, 2H), 6.50–6.45 (m, 2H), 5.37–5.34 (m, 1H), 4.27–4.24 (m, 1H), 3.97 (t, J=6.3 Hz, 2H), 3.87 (s, 3H), 3.42–3.05 (m, 7H), 2.99–2.94 (m, 1H), 1.79–1.75 (m, 2H), 1.47–1.40 (m, 4H), 1.36 (s, 9H). LCMS found for C30H39FN3O10S (M+H)+: m/z=652.

Provenance & Evidence