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ChemicalBook CAS DataBase List Estramustine
2998-57-4

Estramustine synthesis

2synthesis methods
-

Yield: 94.1%

Reaction Conditions:

with dmap;triethylamine in dichloromethane at 40; for 4.5 h;

Steps:


4.00g (14.7mmol)1,3,5(10)-triene-3,17β-estradiol(The compound represented by formula 14) was dissolved in 150.0 mL of dichloromethane,Add 2.97g (29.4mmol) of triethylamine,And 0.19g (1.5mmol) 4-dimethylaminopyridine/DMAP,Stir at room temperature for 10 minutes;Dissolve 4.51g (22.1mmol) of N,N-bis(2-chloroethyl)carbamoyl chloride in 50.0mL of dichloromethane,Slowly add dropwise to the above reaction solution,The dripping is completed within 30 minutes,Continue to stir and react for 1 hour,Then, the reaction solution was transferred to a water bath at 40°C for 3 hours to keep warm. TLC detection reaction shows that the reaction is complete,Stop the reaction,Cool the reaction liquid to room temperature,Add 50.0mL distilled water,Adjust the pH of the reaction solution between 5-6 with 10% hydrochloric acid solution under stirring,Let stand for layering,Separate the organic layer,The aqueous layer was extracted with dichloromethane (50.0mL×3),Combine the organic phases,The solvent was distilled off under reduced pressure to obtain a crude off-white solid.Hot ethanol recrystallization6.09g white crystal compound(Compound represented by formula 15), the yield is 94.1%.

References:

Zhou Yayao CN111410677, 2020, A Location in patent:Paragraph 0047; 0048; 0049

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