O1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[CH2:7][CH2:6]2)[O:4]CC1.Cl>C1COCC1>[N:11]1([CH:8]2[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]2)[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1To a solution of 1 (4.50 g, 19.8 mmol) in THF (100 mL) was added 7 N aqueous HCl (40 mL). The reaction mixture was stirred for 17 h and the reaction was quenched by pouring onto saturated aqueous NaHCO3 (475 mL). The mixture was extracted with ethyl acetate (1×) then CH2Cl2 (3×) and the combined organic extracts dried (MgSO4) and concentrated. The resulting oil was purified by Kugelrohr distillation to give (VII-a) (3.17 g, 87%) as a clear oil; 1H NMR (400 MHz, CDCl3) δ 1.80-1.94 (m, 2H), 1.80-2.10 (m, 2H), 2.30 (m, 1H), 2.45-2.65 (m, 8H), 3.74 (t, J=4.7 Hz, 4H).
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