5-Aminovaleric acid → HCID 42610633, compound

Participants

Reaction Steps

To a solution of 5-aminovaleric acid (12 mg, 100 μmol) in dry DMSO (250 μL) was added N-succinimidyl 4-azido-2,3,5,6-tetrafluorobenzoate (25 mg, 75 μmol). The reaction was allowed to proceed overnight at 45° C. in the dark. The mixture was then acidified with 250 μL of 0.5 N hydrochloric acid and extracted with 400 μL of ethyl acetate three times. The combined extracts were concentrated in vacuo and purified by silica chromatography using 2:1 hexane-ethyl acetate to yield the desired product as a white powder. Yielded: 3 mg, 9 μmol, 12%. TLC: Rf=0.3 (1:1 hexane-ethyl acetate) 1H-NMR (300 MHz, (CD3)2SO): δ 12.03 (s, 1H), 8.89 (t, 1H, J=5.4), 3.23 (q, 2H, J=6.3), 2.22 (t, 2H, 0.1=7.2), 1.497 (m, 4H). ESI-MS m/z: (neg) 333.07 [M−H]−. Calc. 334.23

Provenance & Evidence