[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].OC1CC(=O)NC1=O.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:39][CH2:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]#[N:48])=[CH:43][C:42]=1[O:49][CH3:50]>C1COCC1.C(Cl)Cl>[C:47]([C:44]1[CH:45]=[CH:46][C:41]([CH2:40][NH:39][C:10](=[O:12])[C@@H:9]2[CH2:13][CH2:14][CH2:15][N:8]2[C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])=[C:42]([O:49][CH3:50])[CH:43]=1)#[N:48]
16.0 g of Boc-proline (50 mmol), dissolved in 80 ml of THF, were stirred with 5.7 g of hydroxysuccinimide and 10.2 g of DCC in methylene chloride at 0° C. for 30 min. Then 8.0 g (50 mmol) of 4-aminomethyl-3-methoxybenzenenitrile [sic] dissolved in 50 ml of THF were added dropwise at 0° C., and the mixture was stirred at room temperature for 20 h. The solid was filtered off, the filtrate was mixed with the same volume of ethyl acetate and washed with cooled 5% strength NaHSO4 solution and saturated NaCl solution. 11.5 g (65%) of product were obtained. 1H-NMR (DMSO-d6 ; δ in ppm): 8.38 (m, NH); 7.50-7.35 (m, 3H); 4.40-4.05 (m, 3H, N--CH2 --Ar/N--CH--CO); 3.87 (s, OCH3); 3.50-3.25 (m, 2H, N--CH2); 2.2.5-2.00 [sic] (m, 1H); 1.90-1.65 (m, 3H); 1.40 and 1.30 (2s; 9H)
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