Compound (S)-6
(S)-N-benzyl-3-(3-(but-3-yn-1-yl)-3H-diazirin-3-yl)-N-(1-phenylethyl)propanamide
From: Expedited mapping of the ligandable proteome using fully functionalized enantiomeric probe pairs
View in PubChem | MDL Molfile | Chemdraw file
InChIKey HXPLQWRIOAZPGL-IBGZPJMESA-N
Compound data: NMR
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
The title compound was synthesised following the General Procedure outlined for compound (R)-1. The preparative TLC was run with n-hexane/ethyl acetate 13:7. 29.2 mg (81%) of the product were obtained. 1H NMR (500 MHz, Chloroform-d) (70:30 mixture of rotamers, peaks corresponding to minor rotamer starred) δ 7.39 – 7.17 (m, 8H), 7.14 (m, 0.7H), 7.07 (m, 1.3H), 6.20 (q, J = 7.2 Hz, 0.7H), 5.16* (q, J = 7.0 Hz, 0.3H), 4.96* (d, J = 15.5 Hz, 0.3H), 4.37 (d, J = 17.9 Hz, 0.7H), 4.21 (d, J = 17.9 Hz, 0.7H), 4.00* (d, J = 15.5 Hz, 0.3H), 2.25 (m, 0.7H), 2.08 – 1.79 (m, 6.3H), 1.68 (m, 0.7H), 1.60 (m, 1.3H), 1.48 (d, J = 7.3 Hz, 3H). 13C NMR (126 MHz, CDCl3) δ 172.42, 140.93, 138.09, 128.83, 128.72, 128.53, 128.28, 127.55, 127.51, 127.28, 127.20, 126.58, 125.83, 82.79, 77.29, 77.04, 76.79, 69.06, 51.80, 47.19, 32.55, 28.11, 27.97, 16.96, 13.29. HRMS (m/z) calculated for C23H26N3O [M+H]+: 360.2070; found: 360.2070.
