Hydrochloric Acid → HCID 131726070, compound

Participants

Reaction Conditions

Reaction Steps

At 0° C. the solution of 88 mg (0.2 mmol) of HCl.Lys(ClZ)-OBzl in 5 ml of anhydrous tetrahydrofuran was adjusted to pH 9, to which the pre-cold solution of 38 mg (0.2 mmol) of Boc-Ala-OH, 30 mg (0.22 mmol) of 1-hydroxybenzotriazole and 45 mg (0.22 mmol) of dicyclohexylcarbodiimide in 5 ml of anhydrous tetrahydrofuran was added. The reaction mixture was stirred at 0° C. for 2 h and at room temperature for 5 h and TLC (chloroform/methanol, 30:1) indicated complete disappearance of Boc-Ala-OH. The resulted precipitates of N,N-dicyclohexylurea were filtrated and the filtrate was diluted with 20 ml of ethyl acetate. The solution obtained was washed successively with saturated NaCO3 in water (30 ml×3), saturated NaCl in water (30 ml×3) and KHSO4 in water (5%, 30 ml×3). The separated ethyl acetate layer was dried with anhydrous MgSO4, and then evaporated to provide 112 mg (98%) of the title compound as a colorless powder. Mp94–96° C., FAB-MS (m/e) 575[M+H]+, 475[M-Boc]+.

Provenance & Evidence