Compound 8

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Compound data: 1H NMR

Compound data: 1H NMR

Compound data: 13C NMR

Compound data: 13C NMR

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

The allylic chloride (4.2 mmol), adenosine (1.2 g, 4.6 mmol, 1.1 eq), and sodium iodide (685 mg, 4.6 mmol 1.1 eq) were subsequently added to peptide synthesis grade dimethyl formamide (DMF) (8.4 mL). The resulting turbid reaction mixture was stirred for 24 h whereupon ¹H NMR spectroscopy confirmed full conversion to the allylic chloride. In case the reaction did not go to completion, the mixture was heated to 40 °C for 2 h. The reaction mixture was then concentrated under reduced pressure to obtain a yellow-brown oil. Flash column chromatography (25-30 cm) was used to purify the product. To the crude product, a mixture of CH₂Cl₂ : methanol (80:20) was added, from which pure product precipitated. A white solid (0.82 g, 62% yield) was obtained. Alternatively flash column chromatography was performed using CH₂Cl₂ : methanol (80:20) as the eluent. A white solid (50% yield) was obtained. ¹H NMR (400 MHz, DMSO-d₆) δ 9.97 (s, 1H), 9.17 (s, 1H), 8.76 (s, 1H), 8.72 (s, 1H), 5.94 (d, J = 5.5 Hz, 1H), 5.59 (s, 1H), 5.31 (s, 1H), 5.08 (s, 1H), 4.51 (t, J = 5.3 Hz, 1H), 4.16 (t, J = 4.3 Hz, 1H), 3.98 (q, J = 3.9 Hz, 1H), 3.80 (s, 3H), 3.67 (dd, J = 12.0, 4.0 Hz, 1H), 3.57 (dd, J = 12.0, 4.0 Hz, 1H). ¹³C NMR (101 MHz, DMSO-d₆) δ 150.70, 147.97, 146.76, 142.54, 118.94, 87.68, 85.95, 74.34, 70.13, 61.03, 37.80. ¹H NMR (400 MHz, CD₃OD) δ 8.65 (s, 1H), 8.55 (s, 1H), 6.09 (d, J = 5.1 Hz, 1H), 4.62 (t, J = 5.1 Hz, 1H), 4.34 (t, J = 4.5 Hz, 1H), 4.15 (d, J = 3.5 Hz, 1H), 3.92 (s, 3H), 3.87 (dd, J = 12.2, 3.2 Hz, 1H), 3.78 (dd, J = 12.2, 3.2 Hz, 1H). ¹³C NMR (101 MHz, CD₃OD) δ 152.77, 148.63, 148.55, 144.27, 120.80, 90.38, 87.49, 76.55, 71.84, 62.60, 38.41. HRMS (ESI+, m/z): calculated for C₁₁H₁₆N₅O₄⁺ [M⁺]: 282.1197; found: 282.1199.