Compound 37
((8R,9S,10S)-9-(2',3'-dimethyl-[1,1'-biphenyl]-4-yl)-6-((2-(trifluoromethyl)phenyl)sulfonyl)-1,6-diazabicyclo[6.2.0]decan-10-yl)methanol
From: Substrate-selective inhibitors that reprogram the activity of insulin-degrading enzyme
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Compound data: 1H NMR
Compound data: 13C NMR
Compound data: 19F NMR
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Compound 37 was synthesized using the same routes described for compounds 64, 67 (using 2-(trifluoromethyl)benzenesulfonyl chloride), 69, 71 and 63, consecutively. High resolution mass, calculated for C30H33F3N2O3S [M+H]+ = 559.2237, found 559.2230, Δ = −1.3 ppm. 1H NMR (500 MHz, CDCl3) δ 7.92 (dt, J = 6.4, 3.7 Hz, 1H), 7.86 (dd, J = 5.7, 3.6 Hz, 1H), 7.74 (t, J = 3.4 Hz, 1H), 7.72 (t, J = 3.3 Hz, 1H), 7.34 (t, J = 1.6 Hz, 2H), 7.33 (t, J = 1.8 Hz, 2H), 7.28 – 7.22 (m, 2H), 7.18 (dd, J = 7.6, 1.6 Hz, 1H), 7.14 (t, J = 7.5 Hz, 1H), 7.03 (dd, J = 7.5, 1.6 Hz, 1H), 4.53 (td, J = 10.1, 1.9 Hz, 1H), 4.21 (dd, J = 13.5, 7.8 Hz, 1H), 4.14 (dt, J = 12.6, 2.4 Hz, 2H), 4.06 (dd, J = 13.5, 2.7 Hz, 1H), 3.94 – 3.82 (m, 3H), 3.77 (t, J = 9.8 Hz, 1H), 3.52 (ddd, J = 15.3, 7.9, 3.8 Hz, 1H), 3.19 (ddd, J = 12.8, 7.1, 2.7 Hz, 1H), 2.34 (s, 3H), 2.22 – 2.11 (m, 1H), 2.14 (s, 3H), 2.11 – 1.94 (m, 3H). 19F NMR (471 MHz, CDCl3) δ −57.93, −75.80*. *TFA salt 13C NMR (125 MHz, CDCl3) δ 162.97 (q, J = 36.3 Hz*), 143.29, 141.14, 137.64, 137.51, 134.01, 133.18, 132.80, 132.70, 130.62 (2C), 129.81, 129.36, 129.26 (q, J = 6.0 Hz), 128.31 (q, J = 33.4 Hz), 127.61 (2C), 126.32 (2C), 125.50, 122.58 (q, J = 274.0 Hz *), 72.50, 59.87, 56.73, 50.67, 48.84, 40.29, 29.82, 27.55, 23.14, 20.77, 17.08. *TFA salt
