CC1C=CC(S(O[CH2:12][C:13]2([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:14]2)(=O)=O)=CC=1.C1OCCOCCOCCOCCOCCOC1.[K].[C:43]1(=[O:53])[NH:47][C:46](=[O:48])[C:45]2=[CH:49][CH:50]=[CH:51][CH:52]=[C:44]12>CN(C=O)C>[O:48]=[C:46]1[C:45]2[C:44](=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:43](=[O:53])[N:47]1[CH2:12][C:13]1([NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:14][CH2:15]1To a solution of {1-[(tert-butoxycarbonyl)amino]cyclopropyl}methyl 4-methylbenzenesulfonate (100 g, 293 mmol) in DMF (1000 mL) was added 18-crown-6 (76.8 g, 291 mmol) and phthalimide potassium salt (80.5 g, 435 mmol). The reaction mixture was heated to 50° C. After 3 hours, the reaction mixture was cooled to ambient temperature, quenched with cold water (2000 mL), and filtered to afford crude solids. The solids were washed with petroleum ether (3×200 mL) and dried under reduced pressure to afford tert-butyl {1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]cyclopropyl}carbamate. The material was used without further purification.
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