Dichloroacetic Acid → HCID 10098504, compound

Participants

Reaction Steps

To a solution of 2-(5-benzyloxycarbonylamino-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidinyl)-N-(3,3,3-trifluoro-2-hydroxy-1-isopropylpropyl)acetamide (0.537 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodimide (1.9 g) in toluene (4 mL) and dimethyl sulfoxide (4 mL) was added dichloroacetic acid (0.33 mL) and the resulting solution was allowed to stir for 0.5 h. The reaction mixture was diluted with ethyl acetate, washed (saturated ammonium chloride, water), dried and evaporated to provide a white solid which was collected and washed with ether:hexane (1:1) to give 2-(5-benzyloxycarbonylamino-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidinyl)-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide (0.330 g). Chromatography of the mother liquor with ethyl acetate:dichloromethane (5:95, 10:90) as the eluent gave additional 2-(5-benzyloxycarbonylamino-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidinyl)-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide as a white solid (0.190 g); NMR (DMSO/D2O): 8.46 (s,1), 7.44 (m,10), 5.20 (s,2), 4.54 (m,2 ), 4.05 (d,1), 2.23 (m,1), 0.85 (d,3), 0.75 (d,3); MS: m/z=531(M+1).

Provenance & Evidence