COC1C=CC(S([N:12]2[CH2:17][CH:16]=[CH:15][C@H:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C@@H:13]2[C:24]([OH:26])=O)(=O)=O)=CC=1.Cl.C([NH:35]O)C1C=CC=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C>C(OCC)(=O)C>[C:18]1([CH:14]2[CH:15]=[CH:16][CH2:17][NH:12][CH:13]2[C:24]([NH2:35])=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
To a solution of (+)-(2R*-3R*)-1-(4-methoxybenzenesulfonyl)-3-phenyl-1,2,3,6-tetrahydropyridine-2-carboxylic acid (65 mg, 0.17 mmol) (from Example 20), is added benzylhydroxylamine hydrochloride (32 mg, 0.20 mmol), dicyclohexylcarbodiimide (41 mg, 0.20 mmol) and dimethylaminopyridine (27 mg, 0.22 mmol). The resulting mixture is stirred overnight, diluted with ethyl acetate and filtered through Celite™ and evaporated. The crude product is purified by chromatography elution with 1:1 hexane-ethyl acetate to provide (+)-(2R*-3R*)-N-benzyloxy-1-4-methoxybenzenesulfonyl)-3-phenyl-1,2,3,6-tetrahydropyridine-2-carboxamide.
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