Methyl iodide → 1-(((Tert-butoxy)carbonyl)(methyl)amino)cyclopropane-1-carboxylic acid

To a solution of 1-(tert-butoxycarbonylamino)cyclopropanecarboxylic acid (201 mg, 1.0 mmol) in DMF (2 mL) was added NaH (120 mg, 3.0 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 10 min. before the addition of MeI (568 mg, 4.0 mmol). The mixture was then warmed up to room temperature and stirred for 2 hr. Saturated NH4Cl aqueous solution (20 mL) was added into the mixture, and the solution was extracted with EtOAc (3×10 mL). The combined organic layers were concentrated and the residue was dissolved in MeOH (3 ml) with NaOH (3 N, 1 mL). This mixture was stirred at 80° C. for 1 hr and cooled down to room temperature. The clear solution was purified directly on preparative RP-HPLC to provide 1-(tert-butoxycarbonyl(methyl)amino)cyclopropanecarboxylic acid. ESMS m/z 238.2 (M+Na+).

1. extractionthe solution was extracted with EtOAc (3×10 mL)
2. concentrationThe combined organic layers were concentrated
3. dissolutionthe residue was dissolved in MeOH (3 ml) with NaOH (3 N, 1 mL)
4. stirringThis mixture was stirred at 80° C. for 1 hr
5. temperaturecooled down to room temperature
6. customThe clear solution was purified directly on preparative RP-HPLC

ORD record

ord-ad64136a797d4f0c9eb782c802d9efd3

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08519129B2