Synthesis of potent BCRP inhibitor-Ko143

Tetrahedron Letters

Volumn 49, Issue 9, 2008, Pages 1480-1483

  Li, Yuexian ^a   Hayman, Erik ^b   Plesescu, Mihaela ^a   Prakash, Shimoga R ^a  

^a MILLENNIUM PHARMACEUTICALS INC   (United States)

^b BOSTON COLLEGE   (United States)

Author keywords

Aziridinecarboxylate; BCRP inhibitor; Ko143; Ytterbium triflate

Indexed keywords

ANTINEOPLASTIC AGENT; AZIRIDINE DERIVATIVE; BREAST CANCER RESISTANCE PROTEIN; CARBOXYLIC ACID DERIVATIVE; INDOLE DERIVATIVE; KO 143; TRIFLUOROMETHANESULFONIC ACID; TRYPTOPHAN DERIVATIVE; UNCLASSIFIED DRUG; YTTERBIUM;

ARTICLE; DRUG POTENCY; DRUG SYNTHESIS; OPTICAL ROTATION; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 38649091963     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.12.130     Document Type: Article

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21. Compound 14: General procedure: 1-Benzyl-2-methyl-(S)-1,2-aziridinedicarboxylate and 6-methoxyindole (2 equiv) were dissolved in methylene chloride (3.8 mL/mmol). Ytterbium(III) triflate (1 equiv) was added by portion and the reaction allowed stirring for 24 h. The reaction mixture was washed with water. The organic layer was then dried over magnesium sulfate and rotary-evaporated to dryness. Residue was purified by flash column chromatography on silica gel using a gradient of hexanes and ethyl acetate. Product containing fractions was combined and dried in vacuum to yield 1 as yellow oil (30-60%).
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