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- W2068428086 abstract "Stable label analogues of methotrexate (MTX) and 7-hydroxymethotrexate (7-OH-MTX) were required for use as internal standards for LC/MS quantitation. A minimum incorporation of stable isotopes to produce a mass increase of 3 in the non-glutamate derived portion of the molecule was necessary for adequate MS detection. The commercial availability of des-methyl MTX (aminopterin, 1) made methylation with C2H3I an attractive option. Surprisingly, all attempted methylations of 1 and the dimethyl ester of 1 failed to provide a significant amount of the methylated aniline, apparently due to attenuated reactivity of the secondary amine towards alkylation. However, reductive amination of diacid 1 with C2H2O and NaB2H3CN gave [C2H3]MTX in 52% yield. A previously reported method was utilized to convert [C2H3]MTX to [C2H3]7-OH-MTX. Preparative HPLC purification of [C2H3]7-OH-MTX resulted in extremely low recovery from the column; this was resolved by switching to a column with few free silanols. Copyright © 2002 John Wiley & Sons, Ltd." @default.
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- W2068428086 date "2002-01-01" @default.
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- W2068428086 title "Synthesis of [C2H3]methotrexate and [C2H3]7-hydroxymethotrexate" @default.
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- W2068428086 doi "https://doi.org/10.1002/jlcr.537" @default.
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