Water → dodecyl-3-((1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)carbamoyl)pyrazine-2-carboxylate

Participants

Reaction Steps

Gemcitabine hydrochloride (500 mg, 1.67 mmol), 3-(dodecyloxycarbonyl)pyrazine-2-carboxylic acid (674 mg, 2.01 mmol), (Benzotriazol-1-yl-oxy)tripyrrolidinophosphonium hexafluorophosphate (955 mg, 1.84 mmol), and 4-dimethylaminopyridine (244 mg, 2.0 mmol) were dissolved in N,N-dimethylformamide (10 mL) and stirred at room temperature overnight. The reaction mixture was poured into water, then extracted three times with ethyl acetate. The isolated organic phase was dried with anhydrous Na2SO4. The solvent was removed by vaporizing under reduced pressure. The residue was purified by silica column chromatography (developing agent; dichloromethane/methanol=40/1) to produce 225.7 mg of dodecyl-3-((1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)carbamoyl)pyrazine-2-carboxylate. LC purity 98% (UV 254). LC-MS m/z 582 [M+H]+, (molecular formula: C27H37F2N5O7, molecular weight: 581). The structure and characterization data of the compound were shown in Table 1.

Provenance & Evidence