Reaktionsschritte
To a solution of (C18H37)2NCOCH2OCH2COOH (1.0 g, 1.5 mmol) in CH2Cl2 (30 mL) was added 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (0.31 g, 1.6 mmol) and the reaction was stirred at room temperature. After 0.5 h Gly-Gly-OCH2Ph.TsOH (0.62 g, 1.5 mmol) and Et3N (0.6 mL) were added and the mixture was stirred overnight. The reaction mixture washed with water (20 mL), 0.5 M aqueous HCI (20 mL), water (20 mL), 10% aqueous Na2CO3 (20 mL), and brine (20 mL) then dried over MgSO4, evaporated and the residue crystallized from MeOH to yield (C18H37)2NCOCH2OCH2CO-Gly-Gly-OCH2Ph as a deliquescent white solid (1.32 g, 94%). 1H-NMR (300 MHz, 6, CDCl3) 0.87 (6H, t, J=6.9 Hz), 1.24 (64H, m), 1.48 (4H, bs), 3.05 (2H, t, J=7.5 Hz), 3.22 (2H, t, J=7.5 Hz), 4.06–4.10 (6H, m), 4.28 (2H, s), 5.15 (2H, s), 7.33 (5H, m), 7.51 (1H, t, J=5.7 Hz), 8.23 (1H, t, J=5.7 Hz). 13C-NMR (75 MHz, 6, CDCl3): 14.2, 2.8, 27.0, 27.1, 27.6, 29.5, 29.7, 29.8, 32.0, 41.3, 42.8, 46.9, 67.1, 69.9, 72.2, 128.5, 128.7, 128.9, 135.6, 168.7, 169.9, 170.9.
