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Synthesis of (S)-amino-cvclopropyl-acetic acid methyl ester (4) . A solution of Boc-L-cyclopropylglycine (97 mg, 0.45 mmol) and HCl(cone, 500 mul) in 2,2-dimethoxypropane (5 ml, 40 mmol) was maintained at 40 C overnight. Reaction mixture was evaporated in vacuum. Residue was dissolved in i-PrOH (10 ml) and evaporated in vacuum. The aforementioned procedure was repeated twice. Residue was triturated with ether, filtrated, washed with ether and dried in vacuum overnight to obtained hydrochloric salt of target product (4) (73 mg, 98%) as off-white powder. LC-MS [M+H] 130.0 (C6H11NO2+H, requires 130.17).
tert-butyl (S)-(2-((5-chloro-3-fluoropyridin-2-yl)amino)-1-cyclopropyl-2-oxoethyl)carbamate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
46%
To a solution of (S)-2-((ie/+-butoxycarbonyl)amino)-2-cyclopropylacetic acid (1.0 g, 4.6 mmol, 1.0 equiv) in DCM (50.0 mL) were added EDCI (1.8 g, 9.3 mmol, 2.0 equiv.), HOBt (0.63 g, 4.6 mmol, 1.0 equiv.), and TEA (1.3 mL, 9.3 mmol, 2.0 equiv.). After stirring at r.t. for 5 min, to this mixture was added <strong>[246847-98-3]5-chloro-3-fluoropyridin-2-amine</strong> (0.8 g, 5.6 mmol, 1.2 equiv.). The mixture continued to stir for overnight, concentrated to dryness, diluted with EA, washed with water and brine, dried over Na2S04, concentrated under reduced pressure, and purified by silica gel using EA/HE as eluent to afford 730 mg (46%) of ieri-butyl (S)-(2-((5-chloro-3-fluoropyridin-2-yl)amino)-l-cyclopropyl-2-oxoethyl)carbamate (Intermediate 70-1) as a white solid . LRMS (ES) m/z 344.1 (M+H).
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