Toluene → 2-Amino-4-(3-carboxy-propyl)-imidazole-1-carboxylic acid tert-butyl ester

Temperature

60 °C

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.

1. dissolutionOnce dissolution
2. temperatureThe reaction was then cooled back down to 0° C.
3. customquenched with water (1 mL)
4. temperatureThe resulting viscous solution was warmed to ambient temperature
5. additionCelite® diatomite was added
6. stirringAfter stirring for 5 min
7. filtrationthe mixture was filtered
8. washthe filtrate washed with brine (2×3 mL)
9. dry with materialdried (Na2SO4)
10. customevaporated to dryness
11. customThe crude product was purified via flash column chromatography (2-10% MeOH/CH2Cl2)
12. customto afford pure product

ORD record

ord-acf94d1525b746f19e75fccaa5aefae7

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09084423B2