CC1([C:7]([OH:9])=O)CC(=C)C1.CC[N:12](CC)CC.[N-]=[N+]=[N-].[CH2:20]([OH:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:28]1([CH3:34])[CH:33]=[CH:32][CH:31]=C[CH:29]=1>CCOC(C)=O>[CH3:31][C:32]1([NH:12][C:7](=[O:9])[O:27][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:33][C:28](=[CH2:29])[CH2:34]1To a stirred solution of 1-methyl-3-methylidenecyclobutanecarboxylic acid (2.60 g, 20.6 mmol) in toluene (30 mL) was added Et3N (4.30 mL, 30.9 mmol), followed by diphenylphosphoic azide (6.10 mL, 28.3 mmol). The mixture was stirred at rt for 45 min, then benzyl alcohol (7.60 mL, 73.4 mmol) was added, and the mixture was heated at 80° C. overnight. The mixture was then cooled to rt, diluted with EtOAc (30 mL), washed with sat. NH4Cl (three×40 mL), brine (40 mL), dried over Na2SO4 and concentrated to give the crude title compound as a pale yellow oil. m/z (APCI+) for C14H17NO2232.20 (M+H)+.
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