Invention Grant
US09227948B2 Process for the preparation of 2-substituted-2-(6-(substituted)-7-methylbenzo[D][1,3]dioxol-4-yl)acetic acid derivatives 有权
制备2-取代-2-(6-(取代的)-7-甲基苯并[D] [1,3]间二氧杂环戊烯-4-基)乙酸衍生物的方法

Process for the preparation of 2-substituted-2-(6-(substituted)-7-methylbenzo[D][1,3]dioxol-4-yl)acetic acid derivatives
Abstract:
Present invention relates to an improved and commercial process for the preparation of 2-sustituted-2-(6-(substituted)-7-methylbenzo[d][1,3]dioxol-4-yl)acetic acid derivatives of formula-I the above Formula I, XII, XIII, XV, wherein R1 is a O-protecting group such as methoxymethyl, ethoxymethyl, trialkylsilyl, arylmethyl, tetrahydropyran-2-yl, allyl; X is hydroxyl, halogen, mesylate, triflate, tosylate, acetate; Y is oxygen atom, NH or sulfur atom; R2 is C1-C6 alkyl. 2,4-Dihydroxy-3-methylbenzaldehyde is selectively protected at C-4 position in the form of an ether compound of formula-XII, oxidized the aldehyde function to get the diol of formula-XIII, and condensed with ethyl glyoxalate under Casiraghi reaction conditions to get the compound of formula-XV. Compound of formula-XV is converted to compound of formula-I by conventional chemistry. Compounds of formula-I are key intermediates in the synthesis of ecteinascidines like trabectedin.
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