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(2S,3R)-methyl 2-(2-acetoxy-4-iodobenzamido)-3-hydroxybutanoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
49.2%
To a suspension of L-Threonine methyl ester·HCl ((2S,3R)-methyl 2-amino-3-hydroxybutanoate) (2.45 g, 14.45 mmol) in DCM (195 ml), triethylamine (1.46 g, 14.45 mmol, 2.0 ml) was added. The reaction mixture was stirred at RT for 10 min and 4-iodo salicylic acid (<strong>[16870-28-3]2-hydroxy-4-iodobenzoic acid</strong>) (3.68 g, 13.94 mmol) was added. The solution was cooled to 0 C. and HOBt (0.189 g, 1.4 mmol) and DCC (3.58 g, 17.42 mmol) were added. The reaction mixture was stirred overnight at RT and a precipitate of DCU was formed, which was filtered off (3.4 g). The filtrate was diluted with DCM (60 ml), washed with water (90 ml), saturated NaHCO3 (90 ml), 5% citric acid (90 ml), water (90 ml) and brine (90 ml) and dried over Na2SO4. The organic solvent was evaporated in vacuum and the residue treated with EA (100 ml) and a precipitate of DCU was filtered out (0.2 g). The organic filtrate was evaporated to obtain raw material (5 g). The crude product was purified by flash chromatography: SiO2 (100 ml), CHCl3:Hexane (1:1), CHCl3:Hexane (2:1) to obtain 2.6 g of the title compound. Yield: 49.2%.
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 65℃; for 24h;Sealed tube;
General procedure: In a 50 mL round bottom flask charged with the appropriate salicylic acid derivative (4 mmol), EDC.HCl (5.2 mmol, 1 g), 1-HOBt.xH2O (5.2 mmol, 700 mg) was added DMF (10 mL). The mixture was stirred at room temperature for 1 hour and were added L-threonine methyl ester hydrochloride (4 mmol, 678 mg) dissolved in DMF (10 mL) and the N-methylmorpholine (6 mmol, 0.66 mL). The flask was sealed and the reaction was stirred for 24 hours at 65C. The content was transferred to a separation funnel and the extraction was proceed with aqueous saturated solution of NH4Cl (100mL) and EtOAc (3 x 30 mL). The combined organic phases were washed with water (2 x 100 mL) and brine (100 mL), dried over MgSO4, filtered off and volatiles were evaporated. The crude residue was purified by chromatography column eluting with hexanes/EtOAc (3:2).
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