Hydrochloric Acid → (2S)-6-[(2-anilinoacetyl)amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

Participants

Reaction Steps

The title compound was prepared from Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-L-lysine potassium salt (2.0 g, 5.1 mmol) suspended in a mixture of THF (20 mL), DIEA (1.5 mL, 8.6 mmol) and chioroacetyl chloride (0.8 mL, 10.1 mmol). The reaction mixture was stirred for a period of 30 min. Then, a solution of 2N HCl (20 mL) was added and the solution extracted with EtOAc (25 mL, 3×). The organic phase was dried with MgSO4, filtered and evaporated to a brown oil. The crude material was purified by flash chromatography using a solvent gradient from 39:1 to 19:1 CH2Cl2/MeOH. The product was isolated as a yellowish oil (1.7 g, 78% yield).

Provenance & Evidence