Product name:Paclitaxel EP Impurity I

Synonyms:Benzenepropanoicacid,β-(benzoylamino)-α-hydroxy-,1,1′-[(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxete-6,9-diyl]ester,(αR,α’R,βS,β’S)-

CAS No:2157462-42-3

Molecular formula:C61H62N2O16

Molecular Weight:1079.17

Appearance:white powders

Density 1.42±0.1 g/cm3(Predicted)

Acidity coefficient (PKA) 11.78±0.20(Predicted)

The preparation method of paclitaxel EP impurity I includes the following steps: (1) dissolve 10 DAB (5g, 9.2mmol) in DMF (20ml), add 2-methylimidazole (2.5G, 30.5mmol), stir in low temperature bath (10 ℃), under the protection of nitrogen, drop Triethylchlorosilane (1.5ml, 9mmol), after reaction for 0.5h, add water and dichloromethane to extract the reaction solution, concentrate the organic phase to obtain 14.8g intermediate, the yield is 79.2%(2) The intermediate 1 (4 g, 6.1 mmol) was dissolved in toluene (40 ml), then paclitaxel side chain acid (6.4 g, 24 mmol), 4-dimethylaminopyridine (0.8 g, 6.5 mmol) and N, n ‘- bicyclo chemicalbook hexylcarboimide (8.1 g, 39.3 mmol) were added. After stirring in a low temperature bath (15 ℃) for 3 h, the reaction solution was filtered and the filtrate was concentrated to obtain 26.0 g intermediate in 84.3%(3) The intermediate 2 (6 g, 5.1 mmol) was dissolved in tetrahydrofuran (60 ml) and methanol (60 ml), stirred in cold water bath (10 ℃), hydrochloric acid (1 mol / L, 30 ml) was added dropwise, after reaction for 10 h, saturated sodium bicarbonate solution (60 ml) was added dropwise, heated to 25 ℃ and reacted for 5 h. The reaction liquid was extracted with water and dichloromethane, the organic phase was concentrated and purified by column chromatography, eluted with mobile phase (dichloromethane: methanol = 100:1, V / V), 6 g, and the yield was 83. 3%.