[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN1CCOCC1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[C:41]([O:45][C:46]([N:48]1[CH2:53][CH2:52][C:51]2[O:54][N:55]=[C:56]([C:57](O)=[O:58])[C:50]=2[CH2:49]1)=[O:47])([CH3:44])([CH3:43])[CH3:42]>CN(C)C=O>[N:1]1([C:57]([C:56]2[C:50]3[CH2:49][N:48]([C:46]([O:45][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:47])[CH2:53][CH2:52][C:51]=3[O:54][N:55]=2)=[O:58])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1Piperidine (1.1 ml, 11.18 mmol), N-methylmorpholine (3.68 ml, 33.54 mmol) and BOP reagent (6.42 g, 14.53 mmol) were added to a solution of 5-(tert-butoxycarbonyl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylic acid (3 g, 11.18 mmol) in dry dimethylformamide (100 ml) and the reaction mixture was stirred at room temperature for 16 hours. The solution was then concentrated in vacuo, the residue was taken up in ethyl acetate and the mixture was washed with NaHCO3 solution and NaCl solution. The combined organic phases were dried with Na2SO4, filtered and concentrated in vacuo. Purification was carried out by chromatography on silica gel (100-200 mesh silica gel, 30% ethyl acetate in hexane). The yield was (71%).
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