[CH:1]12[CH:9]([C:10]3[CH:23]=[CH:22][C:13]([O:14][CH2:15][C@H:16]4[O:20][C:19]([NH2:21])=[N:18][CH2:17]4)=[CH:12][CH:11]=3)[CH:5]([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3][CH2:2]2.C([O:26][C:27](=O)[C:28]#[C:29][CH:30]1[CH2:32][CH2:31]1)C>C(O)C>[CH:1]12[CH:9]([C:10]3[CH:23]=[CH:22][C:13]([O:14][CH2:15][C@H:16]4[O:20][C:19]5=[N:21][C:27](=[O:26])[CH:28]=[C:29]([CH:30]6[CH2:32][CH2:31]6)[N:18]5[CH2:17]4)=[CH:12][CH:11]=3)[CH:5]([CH2:4][CH2:3][CH2:2]1)[CH2:6][CH2:7][CH2:8]2To a solution of (S)-5-(4-bicyclo[3.3.1]non-9-yl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine (0.7 g, 2.23 mmol) (Example 20) in ethanol (40 mL) was added 0.462 g (3.35 mmol) of cyclopropyl-propynoic acid ethyl ester (Example 99). The reaction mixture was stirred at 82° C. for 30 minutes. The reaction mixture was concentrated and purified by chromatography on silica gel, eluting with MeOH/CH2Cl2 to afford 0.145 g of the title compound. [α]D25 −10.51 (c 0.5, CHCl3).
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