Compound 30
3-(3-(hex-5-yn-1-yl)-3H-diazirin-3-yl)propan-1-ol
From: A small molecule interacts with VDAC2 to block mouse BAK-driven apoptosis
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Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
To a mixture of 3-(3-(hex-5-yn-1-yl)-3H-diazirin-3-yl)propanoic acid (29) (168 mg, 0.87 mmol) in THF (10 mL) at -10 oC was added N-methylmorpholine (96 μL, 0.87 mmol) followed by isobutyl chloroformate (115 μL, 0.87 mmol). The mixture was stirred for 30 mins then filtered and the filtrate was added dropwise to a stirred solution of sodium borohydride (72 mg, 1.91 mmol) in water (0.5 mL) and stirred for 1 h. The solution was then acidified with 0.1 M HCl and extracted with ethyl acetate, dried with sodium sulfate, filtered and concentrated under reduced pressure. The product was purified using column chromatography using 60 % ethyl acetate/cyclohexane to afford the product 30 (177 mg, 0.78 mmol, 91 %) as a pale yellow oil. 1H-NMR (300 MHz, CDCl3): δ 1.24 (m, 2H), 1.34 (m, 8H), 1.94 (t, J = 2.6 Hz, 1H), 2.15 (td, J = 7.0, 2.6 Hz, 2H), 3.58 (t, J = 6.4 Hz, 2H). LCMS (ES+), m/z = 181.00 [M+H]+.
