Compound 20

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InChIKey FTWIBUPJMRPSCF-LGIYYPAKSA-N

Compound data: CIF

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

To a solution of 90 mg (0.298 mmol, 1 eq.) azido alcohol 13 and 100 μL (0.715 mmol, 2.4 eq.) NEt₃ in CH₂Cl₂ (12 mL) at 0 °C was added dropwise 28 μL (0.358 mmol, 1.2 eq.) MsCl. The reaction mixture was stirred for 2 h at 0 °C and then diluted with sat. aq. NH₄Cl (10 mL). The reaction mixture was extracted with EtOAc (3 × 25 mL) and the combined organic layers were washed with brine (100 mL), dried over MgSO₄, filtered and concentrated in vacuo to yield 96 mg (0.253 mmol, 85%) azido mesylate 20 as a yellow solid (one spot on TLC). TLC (hexanes:EtOAc = 6:4), R_f = 0.45 (UV, CAM). ¹H NMR (CDCl₃, 400 MHz): δ= 7.44–7.32 (m, 5H), 5.92–5.83 (m, 1H), 5.54–5.41 (m, 1H), 5.27–5.09 (m, 2H), 4.74–4.50 (m, 1H), 4.38 (dt, J=9.3, 17.7 Hz, 1H), 3.65 (m, 3H), 3.31–3.20 (m, 2H), 2.91 (s, 2H), 2.33 (s, 2H). ¹³C NMR (CDCl₃, 100 MHz): δ= 156.3, 136.2, 131.7, 131.3, 128.8, 128.5, 128.3, 128.0, 127.4, 80.6, 67.8, 67.6, 61.5, 50.4, 50.4, 47.3, 38.5, 38.0, 28.1, 27.8. IR (Diamond-ATR, neat) ν_max: 2102, 1693, 1467, 1419, 1350, 1255, 1171, 1137, 946, 737 cm^-1. HRMS (EI) calcd for C₁₆H₂₇N₄O₄S: 380.1154; found: 380.1156.