Acetic Acid → HCID 178454187, compound

Participants

Reaction Steps

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).

Provenance & Evidence