Reaction Steps
Boc alcohol (35b) (11.0 g, 27.6 mmol) was dissolved in 4N HCl in dioxan (100 mL, 400 mmol) and the mixture stirred at ambient temperature for 1 hour. The mixture was then concentrated in vacuo and azeotroped three times from toluene to give a pale brown solid (Yield 9.25 g). HPLC-MS 3001 [M+H]+; δH (500 MHz, d6-DMSO) 2.44 (3H, s, CH3-aryl), 3.13 (1H, dd, J=7.8 Hz, NHCH2), 3.38 (1H, dd, J=6.7 Hz, NHCH2), 3.68 (1H, dd, J=2.0, 9.9 Hz, CHOCH2), 3.93 (1H, d, J=5.3 Hz, NHCHCH), 3.98 (1H, dd, J=4.3, 9.9 Hz, CHOCH2), 4.50 (1H, m, NHCHCH), 4.57 (1H, t, J=4.9 Hz, TsOCHCH), 5.03 (1H, in, TsOCHCH), 5.71 (1H, b, NH), 7.52 (2H, d, J=8.0 Hz, aryl), 7.84 (2H, d, J=8.0 Hz, aryl), 9.92 (2H, b, OH+HCl); δC (125 MHz, d6-DMSO) 21.25 (aryl-CH3), 45.99 (NHCH2), 67.60 (NHCH), 72.63 (OCH2CHOH), 75.94 (OCH2CHOH), 77.18 (TsOCHCH), 79.15 (TsOCHCH), 127.84 and 130.40 (aromatic CH), 132.28 (CHOSO2C quaternary), 145.65 (CH3C quaternary).
