C(N1C=CN=C1)(N1C=CN=C1)=O.[O:13]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH2:15][C@H:14]1[C:23](O)=[O:24].[CH3:26][C@:27]12[C@@H:35]([CH3:36])[C@H:31]([NH:32][CH2:33][CH2:34]1)[CH2:30][C:29]1[C:37]([OH:41])=[CH:38][CH:39]=[CH:40][C:28]2=1>ClCCl>[O:13]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH2:15][C@H:14]1[C:23]([N:32]1[CH2:33][CH2:34][C@:27]2([CH3:26])[C@@H:35]([CH3:36])[C@H:31]1[CH2:30][C:40]1[CH:39]=[CH:38][C:37]([OH:41])=[CH:29][C:28]=12)=[O:24]Carbonyldiimidazole (0.47 g) is added to a solution of (S)-2,3-dihydro-benzo[1,4]dioxine-2-carboxylic acid (0.63 g) in dichloromethane (6 mL). The resulting solution is stirred at room temperature for 1 h before (2R,6R,11R)-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-10-ol is added. The solution is further stirred at room temperature overnight. Then, dichloromethane (30 mL) is added and the resulting solution is washed with water. After drying (Na2SO4), the solvent is evaporated to give the product as a white foam-like solid.
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