Hydrochloric Acid → Z-Leu-phe-OH

Participants

Reaction Conditions

Reaction Steps

Dipeptide Ketoacids (General Procedure). To a stirred solution of 0.53 g (1,13 mmol) Z-Leu-Phe-COOEt in 6.0 ml methanol was added 1.27 ml (1.27 mmol) 1M NaOH. The color of the reaction mixture turned dark yellow and a small amount of solid was deposited. The reaction was run at room temperature and progress of the hydrolysis was checked on TLC. After 24 h. no more substrate was detected. The reaction mixture was chilled in one ice bath at 5° C., acidified with 1M HCl to pH=3 and extracted with AcOEt (2×50 mL). The organic extract were washed with 2×50 ml H2O and if necessary, decolorized with carbon and dried over MgSO4. After evaporation of the solvent (rotavaporator), the residue (thick oil) were titurated with 2×25 ml n-hexane and dried in vacuo. Yield 0.39 g (78%) of colorless, very thick oil. TLC, main spot at Rf =0.24, trace of impurity at Rf =0.78, I. Mass spectrum, FB-MS [(M+1)/Z]=441.

Provenance & Evidence