Compound 64
(2R,3S,4S)-1-allyl-3-(4-bromophenyl)-4-((trityloxy)methyl)azetidine-2-carbonitrile
From: Substrate-selective inhibitors that reprogram the activity of insulin-degrading enzyme
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Compound data: 1H NMR (source A)
Compound data: 1H NMR (source B)
Compound data: 13C NMR (source B)
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Samples of azetidine-core intermediate 64 were obtained from the Broad Institute (source A) and additionally generated at WuXi AppTec (source B) according to the route reported in Journal of Organic Chemistry 2012, 77 (17), 7187-7211, where this compound is numbered “5d”, page 7188. Comparison of 1H-NMR spectra from the two respective samples showed no differences and indicated similar purity of >95%. High resolution mass, calculated for C33H29BrN2O [M+H]+ = 549.1536, found 549.1540, Δ = 0.73 ppm. 1H NMR (600 MHz, CDCl3) δ 7.50 – 7.48 (m, 1H), 7.48 – 7.47 (m, 1H), 7.46 – 7.44 (m, 3H), 7.44 – 7.42 (m, 3H), 7.34 – 7.29 (m, 6H), 7.28 (t, J = 1.3 Hz, 1H), 7.27 – 7.25 (m, 2H), 7.13 – 7.12 (m, 1H), 7.12 – 7.10 (m, 1H), 5.88 (dddd, J = 17.3, 10.1, 7.4, 5.7 Hz, 1H), 5.34 (dq, J = 17.0, 1.5 Hz, 1H), 5.24 (dq, J = 10.2, 1.2 Hz, 1H), 3.71 (t, J = 7.9 Hz, 1H), 3.62 (d, J = 8.2 Hz, 1H), 3.52 (ddt, J = 13.0, 5.7, 1.4 Hz, 1H), 3.43 – 3.39 (m, 1H), 3.39 (dd, J = 13.0, 5.2 Hz, 1H), 3.33 – 3.28 (m, 1H), 3.17 (dd, J = 13.1, 7.4 Hz, 1H). 13C NMR (100 MHz, CDCl3) δ 206.35, 143.81 (3C), 136.75, 132.77, 131.98 (2C), 128.87 (2C), 128.73 (6C), 128.00 (6C), 127.26 (3C), 121.72, 119.89, 119.23, 87.08, 69.23, 66.37, 60.55, 55.31, 44.69.
