Sodium Chloride → HCID 86693760, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Boc-D-Aspartic acid-1-benzyl ester (0.250 g, 0.77 mmol) taken in THF (4 mL), cooled to −10° C., Ethyl chloroformate (0.11 ml, 1.1 mmol) and TEA (0.34 ml, (2.47 mmol) was added and stirred for 30 min. NaN3 (0.25 g, 0.386 mmol) was dissolved in water (4 ml) and added portion wise to the reaction mixture maintaining the temperature at −10° C. The reaction mixture was slowly warmed to room temperature and stirred for further 2 h. After completion of reaction (by TLC), the reaction mixture was poured into saturated NaCl solution and extracted with EtOAc (2×10 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to half of the volume; PhMe (15 mL) was added and heated to 80° C. for 4 h. After completion (by TLC), the reaction mixture was poured into saturated NaCl solution and extracted with EtOAc (2×15 mL). The combined organic extracts were dried over Na2SO4 and purified by column chromatography to afford 25a (0.11 g, 44%) as a brown sold.

Provenance & Evidence