[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].Cl.O.ClC(OCC(C)C)=O.Cl.NC1C=C(C(O)=O)C(O)=CC=1.CC(O)=O>CN(C=O)C.CO.CCCCO>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9]
381.1 Grams (1.16 mol) of BOC-Arg-OH.HCl.H2O was dissolved in 1,392 ml of DMF, and then 151 ml of NEM was added thereto, followed by dropwise addition of 152.3 ml of isobutyl chloroformate at -20° C. After 10 minutes reaction, a 928 ml DMF solution of 219.8 g (1.16 mol) of 5-aminosalicylic acid hydrochloride and 301.6 ml of NEM was added dropwise to said reaction mixture at -15° to -10° C. The reaction was continued for 3 hours at the same temperature and additionally continued for 15 hours at room temperature. After the reaction was completed, the DMF was removed by evaporation under a reduced pressure and the residue obtained was dissolved in 464 ml of MeOH and 332 ml of n-BuOH. To the mixture was added with 3,300 ml of AcOH, washed twice with 2,160 ml of cold 5% hydrochloric acid saturated with sodium chloride, then dried with anhydrous magnesium sulfate. After drying, the magnesium sulfate was removed by filtration and the solvent was removed by evaporation under a reduced pressure to obtain 464.8 g (89.9%) of BOC-Arg-CHA.HCl. Rf1 =0.64. Melting point: 225.0° C. (decomposed). [α]D20 -10.7 (C=1, MeOH).
Wird geladen…
