[CH2:1]([C@H:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:10][C@H:9]1[OH:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]([O:31][C:32]([NH:34][CH2:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](O)=[O:41])=[CH:38][CH:37]=1)=[O:33])([CH3:30])([CH3:29])[CH3:28].Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([C@H:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][C:40](=[O:41])[C:39]3[CH:38]=[CH:37][C:36]([CH2:35][NH:34][C:32]([O:31][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:33])=[CH:44][CH:43]=3)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:10][C@H:9]1[OH:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1To a solution of 500 mg (1.33 mmol) (3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenol in 10 ml methylenechloride were added 368 mg (1.46 mmol) 4-(tert-butoxycarbonylamino-methyl)-benzoic acid, 16.3 mg (0.133 mmol) DMAP und 511 mg (2.66 mmol) N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride and the reaction mixture was stirred at 0° C. After 1 hour, 0.5 N HCl was added and the aqueous layer was extracted with methylenechloride. The combined organic layers were washed with 0.5N HCl solution and brine, dried over NaSO4, filtered and the solvent was removed under reduced pressure to give the crude product. Crystallization from diethylether yielded 280 mg (0.460 mmol, 35%) 4-(tert-butoxycarbonylamino-methyl)-benzoic acid (3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl ester as colorless crystalls.
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