Citric Acid → HCID 57504587, compound

Participants

Reaction Steps

A solution of 1-chloro-N,N,2-trimethylprop-1-en-1-amine (1.55 mL, 11.7 mmol) in DCM (5 mL) was added dropwise to a stirred solution of (S)-2-(tert-butyldimethylsilyloxy)-3-methoxypropanoic acid C4c (2.5 g, 10.7 mmol) in DCM (15 mL) under nitrogen. The resulting solution was stirred at ambient temperature for 30 minutes. N-Ethyl-N-isopropylpropan-2-amine (2.74 mL, 16.0 mmol) was added in one portion followed by 5-methylpyridin-2-amine (CAS 1603-41-4) (1.27 g, 11.73 mmol) in DCM (5 mL) dropwise. The resulting solution was stirred at ambient temperature for 1 hour. 1M Citric acid (10 mL) was added and the mixture extracted with EtOAc (20 mL). The organic phase was washed with water (5 mL) and brine (5 mL), dried over MgSO4, filtered and evaporated to provide the crude product. Purification by flash silica chromatography, elution gradient 20 to 100% EtOAc in isohexane furnished (S)-2-(tert-butyldimethylsilyloxy)-3-methoxy-N-(5-methylpyridin-2-yl)propanamide (1.4 g). 1H NMR (400 MHz, CDCl3) δ 0.2 (6H, s), 1.01 (9H, s), 2.32 (3H, s), 3.41 (3H, s), 3.66-3.75 (2H, m), 4.40-4.42 (1H, m), 7.52 (1H, d), 7.14-7.16 (2H, m), 9.04 (1H, s), m/z (ESI+) (M+H)+=326; HPLC tR=2.75 min.

Provenance & Evidence