Hydrochloric Acid → HCID 88139793, compound

Participants

Reaction Steps

D,L-Homocysteine (6.0 g, 44.3 mmol) in 2N NaOH (28.8 mL, 57.7 mmol, 1.3 equiv) is stirred at 0° C. under an argon atmosphere. A solution of 2-bromopropanol (6.66 g, 53.3 mol, 1.2 equiv) in ethanol (50 mL) is slowly added dropwise at 0 C. The resulting solution is stirred overnight at room temperature and then the mixture is acidified to pH˜6 with 1 N HCL. The solvent is removed under reduced pressure to leave a thick oil. The penicillamine adduct is then dissolved in dioxane (100 mL) and water (100 mL) and stirred at room temperature. Triethylamine (13.5 g, 133.2 mmol, 3 equiv) is then added to the reaction mixture followed by 4-methoxyphenylsulfonyl chloride (10.0 g, 48.8 mmol. 1.1 equiv). The resulting homogeneous solution is stirred at room temperature for 18 hours and then acidified to pH˜2 with 1N HCl. The solution is poured into water and extracted with methylene chloride. The organic extracts were dried (MgSO4) and concentrated to an oil under reduced pressure. The resulting oil is diluted in methanol (30 mL) and enough diazomethane in diethyl ether is added to form a yellow solution. The mixture is concentrated under reduced pressure to leave a colorless oil. Purification of the resulting methyl ester is accomplished by chromatography on silica gel using 1/1 hexane/EtOAc as the eluent. The desired product is obtained as a clear, colorless oil. MS (ESI): 364 (M+H+), 381 (M+NH4+).

Provenance & Evidence