C1O[C:4]2([CH2:11][CH2:10][CH:9]3[CH2:12][CH:5]2[CH2:6][CH2:7][CH:8]3[NH:13][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[O:3]C1.Cl>CC(C)=O>[CH2:17]([O:16][C:14](=[O:15])[NH:13][CH:8]1[CH2:7][CH2:6][CH:5]2[CH2:12][CH:9]1[CH2:10][CH2:11][C:4]2=[O:3])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1915 mg of 6-Benzyloxycarbonylamino-bicyclo[3.3.1]nonan-2-one ethylene ketal (99) were suspended in 7.6 mL of acetone and 2.9 mL of 5N HCl were added. The mixture was stirred for 2 h, the acetone was evaporated and the remaining liquid was slowly added to sat. NaHCO3. The aqueous layer was extracted with dichloromethane three times. The combined organic layer was dried over sodium sulfate and evaporated to dryness to give 0.79 g of the desired product. Rt=2.87 min (Method E). Detected mass: 288.2 (M+H+).
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