C[Al](C)C.C1(C)C=CC=CC=1.[C:12]([O:16][C:17]([N:19]1[CH:23]=[C:22]([CH2:24][CH2:25][CH2:26][C:27]([O:29]C)=[O:28])[N:21]=[C:20]1[NH2:31])=[O:18])([CH3:15])([CH3:14])[CH3:13]>ClCCCl.ClCCl>[C:12]([O:16][C:17]([N:19]1[CH:23]=[C:22]([CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])[N:21]=[C:20]1[NH2:31])=[O:18])([CH3:15])([CH3:13])[CH3:14]
To a stirring 0° C. solution of amine (0.704 mmol) in anhydrous 1,2-dichloroethane (1 mL) was added drop-wise a 2M solution of AlMe3 in PhCH3 (0.351 mL, 0.704 mmol). The solution was stirred for 10 min before the addition of 2-amino-4-(3-methoxycarbonyl-propyl)-imidazole-1-carboxylic acid tert-butyl ester 18 (100 mg, 0.352 mmol) in several portions. Once dissolution was complete, the reaction was warmed to 60° C. and stirred until completion as evident by TLC analysis. The reaction was then cooled back down to 0° C. before being diluted with dichloromethane (5 mL) and quenched with water (1 mL). The resulting viscous solution was warmed to ambient temperature and Celite® diatomite was added. After stirring for 5 min, the mixture was filtered and the filtrate washed with brine (2×3 mL), dried (Na2SO4), and evaporated to dryness. The crude product was purified via flash column chromatography (2-10% MeOH/CH2Cl2) to afford pure product.
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