[CH:1]1[C:6]([CH2:7][C@H:8]([NH2:12])[C:9]([OH:11])=[O:10])=[CH:5][CH:4]=[C:3]([N:13]([CH2:17][CH2:18][Cl:19])[CH2:14][CH2:15][Cl:16])[CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:26](OC(=O)C)(=[O:28])[CH3:27].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.O1CCOCC1>[CH3:27][C:26]([NH:12][CH:8]([C:9]([OH:11])=[O:10])[CH2:7][C:6]1[CH:5]=[CH:4][C:3]([N:13]([CH2:14][CH2:15][Cl:16])[CH2:17][CH2:18][Cl:19])=[CH:2][CH:1]=1)=[O:28]600 mg of melphalan (63) is suspended in 25 ml of water containing 500 mg of sodium carbonate. 10 ml of dioxane is added and 1 ml of acetic anhydride. After stirring at ambient temperature for 1 h citric acid is added and the mixture extracted with ethyl acetate. After washing with water and brine the organic phase is dried (sodium sulfate) and concentrated in vacuum. Removal of all volatiles yields the crude N-acetylmelphalan that is carried on to the next step without further purification.
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