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

Participants

Reaction Steps

Gemcitabine hydrochloride (0.7 g, 2.34 mmol), 2-(dodecyloxycarbonyl)benzoic acid (1.02 g, 3.04 mmol), (Benzotriazol-1-yl-oxy)tripyrrolidinylphosphonium hexafluorophosphate (1.34 g, 2.57 mmol), and 4-dimethylaminopyridine (428 mg, 3.51 mmol) were dissolved in N,N-dimethylformamide (10 mL) and stirred overnight at room temperature. The reaction mixture was poured into water, and 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=30/1) to produce 362.5 mg of Dodecyl-2-((1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)carbamoyl)benzoate. LC purity 98% (UV254). LC-MS m/z 580 [M+H]+ (molecular formula: C29H39F2N3O7, molecule weight: 579). The structure and characterization data of the compound were shown in Table 1.

Provenance & Evidence