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3-[4-(alkoxy) phenyl] propionate compound and preparation method and application thereof
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A compound and propionate technology, applied in the field of medicinal chemistry, can solve the problems of "three wastes" discharge, harsh reaction conditions, cumbersome reaction operation and post-treatment process, etc.
Inactive Publication Date: 2013-05-22
SICHUAN UNIV
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[0011] The above-mentioned method for synthesizing 3-(2,3-dihydrobenzofuran-5-yl)-propionic acid (II) has expensive raw materials, harsh reaction conditions, cumbersome reaction operations and post-treatment processes, and partial yields. Low, serious discharge of "three wastes" in the preparation process, etc., make the synthesis cost of compound (II) higher, and the large-scale preparation is limited
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Embodiment 1
[0042] Preparation of methyl 3-[4-(2,2-diethoxyethoxy)phenyl]propionate (Ia)
[0043] Add 18.1 g (0.1 mol) of methyl 3-(4-hydroxyphenyl) propionate, 23.5 g (0.12 mol) of bromoacetal, anhydrous K 2 CO 3 16.5g (0.12mol) and 150ml of acetone, heated and refluxed and stirred for 15h, after the reaction, filtered, the filtrate was evaporated to remove the solvent under reduced pressure, and the residual oil was dissolved in 120ml of chloroform, followed by 40ml of 10% aqueous sodium hydroxide solution, saturated NaCl aqueous solution 40ml washed, the organic layer was washed with anhydrous NaCl 2 SO 4 Dry, filter, and evaporate the solvent under reduced pressure to obtain 28.16 g of methyl 3-[4-(2,2-diethoxyethoxy) phenyl] propionate, with a yield of 95.0%; ESI-MS (m / z ,+Q): 297.1[M+H] + .
Embodiment 2
[0045] Preparation of isopropyl 3-[4-(2-oxyethoxy)phenyl]propionate (Ib)
[0046] The operation is the same as in Example 1, except that methyl 3-(4-hydroxyphenyl) propionate is replaced by isopropyl propionate 3-(4-hydroxyphenyl), and bromoacetal is replaced by 40% monochloroacetaldehyde Aqueous solution is replaced, and acetone is replaced with N,N-dimethylformamide, obtains 3-[4-(2-oxyethoxy) phenyl] isopropyl propionate, yield 80.5%; ESI-MS (m / z, +Q): 251.0 [M+H] + .
Embodiment 3
[0048] Preparation of Cyclohexyl 3-[4-[(1,3-dioxan-2-yl)methoxy]phenyl]propionate (Ic)
[0049] The operation process is the same as in Example 1, except that 3-(4-hydroxyphenyl) methyl propionate is replaced with 3-(4-hydroxyphenyl) cyclohexyl propionate, and bromoacetal is replaced with 2-(bromomethyl base)-1,3-dioxane instead, acetone was replaced by THF, anhydrous K 2 CO 3 Substituted by pyridine, 3-[4-[(1,3-dioxan-2-yl)methoxy]phenyl]cyclohexyl propionate was obtained in a yield of 91.8%; ESI-MS (m / z, +Q): 335.0[M+H] + .
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Abstract
The invention belongs to the field of pharmaceutical chemistry, and in particular relates to a 3-[4-(alkoxy) phenyl] propionate compound with a structural formula as below, and a preparation method and application thereof. The 3-[4-(alkoxy) phenyl] propionate compound can be used for preparing 3-(2,3-dihydrobenzofuran-5-yl)-propionic acid. In the structural formula, R1 represents free aldehyde group or-CH (OR3OR4), and R3 and R4 independently represent H, C1-12 straight chain alkyl or branched chain alkyl or cycloalkyl, or R3 and R4 are connected to form cyclic acetal; and R2 represents C1-12straight chain alkyl or branched chain alkyl or cycloalkyl, allyl, benzyl and substituted benzyl, wherein when R2 is methyl, R1 is not the free aldehyde group.
Description
technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to 3-[4-(alkoxy)phenyl]propionate compound (I), its preparation method and preparation method of 3-(2,3-dihydrobenzofuran-5 -yl)-propionic acid (II) application. [0002] [0003] Where: R 1 Indicates a free aldehyde group or -CH(OR 3 OR 4 ), R 3 and R 4 Each independently represents H, C 1-12 straight chain alkyl or branched chain alkyl or cycloalkyl, or R 3 and R 4 Linked to form a cyclic acetal; R 2 means C 1-12 straight chain alkyl or branched chain alkyl or cycloalkyl, allyl, benzyl, substituted benzyl; where, R 2 When it is methyl, R 1 Not free aldehyde groups. Background technique [0004] 3-(2,3-Dihydrobenzofuran-5-yl)-propionic acid (II) is an important intermediate in the synthesis of selective melatonin receptor agonist - Ramelteon (Ramelteon), literature: J Med Chem 2002, 45(19), 4222; WO2006030739; WO 2008150953; WO 2008151170, etc., describe the prepara...
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