C(P(=O)(OCC)OCC)#N.[NH2:11][C:12]1[C:13]([O:24][CH2:25][C@@H:26]([C:35]([OH:37])=O)[NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1.CN(C=O)C>CCOC(C)=O>[O:37]=[C:35]1[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:13]=2[O:24][CH2:25][C@@H:26]1[NH:27][C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34]0.136 ml of diethyl cyanophosphonate (147.8 mg, 0.906 mmol) is introduced, at 0° C., into a 25 mL three-necked flask containing 284 mg of 36 (0.763 mmol) and 6.2 mL of DMF, followed 10 minutes later by 0.102 ml of TEA (0.731 mmol). The reaction medium is stirred at 0° C. for 2 h. 20 ml of AcOEt are added and then the mixture is washed with twice 20 mL of distilled water. The organic phase is dried over MgSO4, filtered and then evaporated to dryness. 160 mg of expected product 37 are obtained.
読み込み中…