Benzylamine → HCID 7201487, compound

Participants

Reaction Conditions

Reaction Steps

Into a 500 mL round bottomed flask equipped with a magnetic stirrer was added N-(tert-butoxycarbonyl)-L-isoleucine (22.53 g, 97.39 mmol, 1.0 eq) and THF (300 mL). The solution was stirred until homogeneous, cooled to -5° C., and treated with N-ethylmorpholine (14.23 mL, 12.88 g, 112.0 mmol, 1.15 eq). The solution was stirred at -5° C. for 20 min, and isobutyl chloroformate (13.24 mL, 13.90 g, 102 mmol, 1.05 eq) was added dropwise over 10 min. After stirring at -5° C. for 30 min, benzylamine (12.24 mL, 12.0 g, 112.0 mmol, 1.15 eq) was added dropwise over 10 min. After the addition was complete, the flask was removed from the cold bath and the solution was stirred at 22° C. for 2.5 hrs. The solution was concentrated to a residue, and partitioned between ethyl acetate (200 mL) and water (100 mL). The aqueous layer was extracted with ethyl ether (2×100 mL) and discarded. The organic extracts were combined, washed with 1N HCl (5×50 mL), 1N NaOH (3×50 mL), satd. aq NaCl (50 mL), and dried (MgSO4). The solution was concentrated in vacuo to provide 29.93 g (96%) of N-(tert-butoxycarbonyl)-L-Isoleucine benzylamide as a white solid.

Provenance & Evidence