Acetate → 2-(2-Guanidinoethoxy)ethyl acetate

Reaction equation

C(O)(=O)C[CH2:3][C:4]([OH:6])=[O:5].O[CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][C:16]([NH2:18])=[NH:17].C(OC(=O)C)(=O)C.C([O-])(=O)C>C(N(CC)CC)C>[C:4]([O:6][CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][C:16]([NH2:18])=[NH:17])(=[O:5])[CH3:3]

Participants

Procedure

2.06 g (9.99 mmol) of 2-(2-hydroxyethoxy)ethylguanidine succinate, 8 ml of triethylamine, 0.122 mg (1.0 mmol) of 4-N,N-dimethylaminopyridine and 1.02 g (9.99 mmol) of acetic anhydride were placed in a 50 ml two neck flask and were stirred for 1 hour at room temperature. After the upper phase was removed by decantation, the obtained crude product was washed five times with 50 ml of diethylether. The product was purified by a silica gel column chromatography (eluent, chloroform/ethanol=2/1 containing 0.5% acetic acid) to obtain 1.00 g of the title compound (starch syrup-like, 4.0 mmol, 40.0% in yield) in the form of acetate. Results of the analysis of this compound are as follows.