1,2-Dichloroethane → HCID 15885802, compound

Participants

Reaction Conditions

Reaction Steps

To an ice cooled suspension of CDI (0.53 g, 3.27 mmol) in 5 mL of pyridine was added L-alanine t-butyl ester hydrochloride (0.57 g, 3.13 mmol). After stirring at 0° C. for 30 minutes, 2-amino-6-methylbenzoic acid (0.43 g 2.85 mmol) was added. The ice bath was removed and the reaction was stirred at 65° C. for 2 hours. The reaction mixture was diluted with EtOAc and washed with 1N HCl, dried (MgSO4), filtered and evaporated under reduced pressure. The crude product (0.30 g) was dissolved in 5 mL of CH2Cl2. Triethylamine (0.15 g, 1.47 mmol) and EDC (0.28 g, 1.47 mmol) were added sequentially. After stirring at room temperature for 2 hours the reaction mixture was diluted with EtOAc and washed with 1N HCl, dried (MgSO4), filtered and evaporated under reduced pressure. Silica gel chromatography of the residue (1:1 EtOAc/hexane) afforded 113 mg of N-(5-methyl-4-oxo-4H-3,1-benzoxazin-2-yl)-L-alanine, t-butyl ester: Anal. Calc'd. for C16H20N2O4: C, 63.14; H, 6.62; N, 9.21. Found: C, 62.90; H, 6.97; N, 9.11. 1H-NMR (300 MHz, CDCl3) δ 1.49 (s, 9H), 1.50 (d, J=7 Hz, 3H), 2.70 (s, 3H), 4.48 (pent, J=7 Hz, 1H), 5.68 (br. s, 1H, exchangeable), 6.95 (d, J=8 Hz, 1H), 6.99 (d, J=8 Hz, 1H), 7.45 (t, J=8 Hz, 1H).

Provenance & Evidence