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14 Amine (2 mmol) and aldehyde (2 mmol) were dissolved in 3 mL of a 1:1 mixture of CH2Cl2 and EtOH. After 30 min stirring at r.t. pyruvic acid derivative (2 mmol) was added. The mixture was stirred for 16 h. The solvent was removed and the remainder taken up in Et2O for solidifying. Compounds 4, 5 and 6 could be used for the next step without purification. All other compounds were purified via preparative HPLC (column Grom-Sil 120 ODS-5, 10 × 4 cm, 10 µm, flow 50 mL/min, gradient 20-100% A in 15 min, solvent A = MeOH + 0.5% AcOH, solvent B = H2O + 0.5% AcOH). Yields of 1-8 are given in Table
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16 Compound 1 (250.8 mg, 0.6 mmol) was dissolved in 5 mL of anhydrous CH2Cl2 together with N,N-dimethylamino-pyridine (15.9 mg, 0.13 mmol). Then, N-cyclohexyl-N′-methyl polystyrene (Novabiochem, 750 mg, 1.2 mmol) was added and the mixture agitated overnight at r.t. Resin was filtered off and thoroughly washed with CH2Cl2. The combined solvents were evaporated and the remainder was subjected to preparative HPLC (column Waters SunFire Prep C18 OBD, 19 × 50 mm, 5 µm, flow 30 mL/min, gradient 20-90% A in 15 min, solvent A = MeOH + 0.03% formic acid, solvent B = H2O + 0.03% formic acid). Yield of 9: 60 mg (25%), 17: 28 mg (5.8%), 25: 6 mg (0.8%).
Compound 9: 1H NMR (400 MHz, CDCl3): δ = 1.05 (9 H, s, CH3), 1.10-1.80 (6 H, m, CH2CH2CH2), 2.79-2.88 (1 H, t, CH of CH2, J = 13.3 Hz), 3.51-3.61 (1 H, t, CH′ of CH2, J = 13.3 Hz), 4.02-4.14 (2 H, m, CH2), 4.76-4.82 (1 H, d, CH of CH2, J = 17.2 Hz), 4.92-4.98 (1 H, d, CH′ of CH2, J = 17.2 Hz), 6.06 (1 H, s, CH), 6.76-6.88 (3 H, m, Harom), 7.16-7.22 (1 H, d, J = 8.6 Hz, Harom). 13C NMR (100 MHz, CDCl3): δ = 24.3, 25.4, 25.8, 26.1, 40.5, 43.0, 54.2, 64.4, 67.7, 110.2, 118.1, 122.0, 124.8, 127.0, 129.8, 154.5, 155.5, 164.5, 168.9, 202.5.
Compound 17: 1H NMR (400 MHz, DMSO-d
6): δ = 1.10 (18 H, s, CH3), 1.14-1.68 (12 H, m, 2 × CH2CH2CH2), 3.30-3.54 (4 H, m, 2 × CH2), 4.06-4.18 (4 H, m, 2 × CH2), 4.83-4.93 (4 H, m, 2 × CH2), 5.83 (2 H, s, 2 × CH), 6.70-6.78 (2 H, m, Harom), 6.85-6.92 (2 H, m, Harom), 6.95-7.03 (2 H, m, Harom), 7.17-7.26 (2 H, m, Harom). 13C NMR (100 MHz, DMSO-d
6): δ = 22.4, 24.6, 25.3, 27.0, 40.1, 42.5, 54.1, 64.3, 67.3, 110.0, 118.5, 122.1, 125.2, 127.4, 129.9, 156.0, 156.3, 165.0, 168.5, 202.7.
Compound 25: No NMR spectra could be recorded due to lack of substance.
17
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