Diisopropylethylamine → 2-(acetylamino)-3-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]-N-(4-phenylbutyl)propanamide

Participants

Reaction Steps

To a solution of (2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]propanoic acid (12 mg, 0.035 mmol) in N,N-dimethylformamide (1.0 mL) was added N,N-diisopropylethylamine (0.018 mL, 0.10 mmol) and N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (16 mg, 0.042 mmol) and premixed for 5 minutes. 4-phenylbutan-1-amine (6.3 mg, 0.042 mmol) was added and the mixture was stirred for 2 h. The product was purified by preparative LCMS to afford the final product (6.8 mg, 41%). 1H NMR (500 MHz, CD3OD): δ 7.41 (d, J=8.3 Hz, 2H), 7.33 (d, J=8.3 Hz, 2H), 7.25–7.27 (m, 2H), 7.15–7.20 (m, 4H), 5.08–5.12 (m, 1H), 4.54–4.58 (m, 1H), 3.18–3.31 (m, 1H), 3.07–3.17 (m, 3H), 2.93–2.97 (m, 1H), 2.59–2.68 (m, 2H), 1.94 (s, 3H), 1.51–1.59 (m, 2H), 1.41–1.46 (m, 2H); LCMS found for C24H30N3O5S (M+H)+: m/z=472.2

Provenance & Evidence