ChemicalBook CAS DataBase List METHYL 4-(4-(BIS(2-CHLOROETHYL)AMINO)PHENYL)BUTYRATE

METHYL 4-(4-(BIS(2-CHLOROETHYL)AMINO)PHENYL)BUTYRATE synthesis

11synthesis methods

Product Name:METHYL 4-(4-(BIS(2-CHLOROETHYL)AMINO)PHENYL)BUTYRATE
CAS Number:79481-83-7
Molecular formula:C15H21Cl2NO2
Molecular Weight:318.2387

67-56-1 Synthesis

67-56-1
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METHYL 4-(4-(BIS(2-CHLOROETHYL)AMINO)PHENYL)BUTYRATE

79481-83-7
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Yield:79481-83-7 95%

Reaction Conditions:

in dichloromethane at 15 - 20; for 3 h;Inert atmosphere;

Steps:

4.1.3. 4-(4-(Bis(2-chloroethyl)amino)phenyl)butan-1-ol (3)

Compound 1 (15.5 mmol, 1.0 equiv.) was dissolved in DCM (125 mL) and methanol (75 mL, 3 vol) was slowly added over aperiod of 1 h at 15-20 °C. The reaction mixture was stirred at ambient temperature for 2 h. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate (125 mL, 5 vol) and washed successively with a 5% aq. NaHCO3. Evaporation of the solvent under reduced pressure resulted in the chlorambucil methyl ester (16.4 mmol,1.0 equiv.) in 95% yield as a light brown oil, which was added to a suspension of lithium aluminium hydride (32.8 mmol, 2 equiv.) in anhydrous THF (100 mL, 4 vol) at 0-5 °C for a period of 1 h. The reaction mixture was thereafter allowed to stirat ambient temperature for 2-3 h. Next, the reaction mixture wascooled to 0-5 °C and quenched slowly with ethyl acetate (250 mL, 10 vol) followed by water (100 mL, 4 vol). The reaction mixture was filtered through celite and ethyl acetate (50 mL, 2 vol) was used to wash the celite bed. The organic layer was washed with water (100 mL, 4 vol), dried over anhydrous Na2SO4, and filtered. Evaporationof the solvent under reduced pressure resulted in 99% yield of the crude alcohol as a pale yellow oil, which was used in the next step.

References:

van Kuijk, Simon J.A.;Parvathaneni, Nanda Kumar;Niemans, Raymon;van Gisbergen, Marike W.;Carta, Fabrizio;Vullo, Daniela;Pastorekova, Silvia;Yaromina, Ala;Supuran, Claudiu T.;Dubois, Ludwig J.;Winum, Jean-Yves;Lambin, Philippe [European Journal of Medicinal Chemistry,2017,vol. 127,p. 691 - 702]