methyl 5-chloro-4-[(4-methoxybenzyl)oxy]-2-[(2S)-oxiran-2-ylmethoxy]benzoate

Base Information

• Chemical Name: methyl 5-chloro-4-[(4-methoxybenzyl)oxy]-2-[(2S)-oxiran-2-ylmethoxy]benzoate
• CAS No.: 644971-06-2
• Molecular Formula: C₁₉H₁₉ClO₆
• Molecular Weight: 378.809

Synonyms:methyl 5-chloro-4-[(4-methoxybenzyl)oxy]-2-[(2S)-oxiran-2-ylmethoxy]benzoate

Chemical Property of methyl 5-chloro-4-[(4-methoxybenzyl)oxy]-2-[(2S)-oxiran-2-ylmethoxy]benzoate

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Technology Process of methyl 5-chloro-4-[(4-methoxybenzyl)oxy]-2-[(2S)-oxiran-2-ylmethoxy]benzoate

There total 2 articles about methyl 5-chloro-4-[(4-methoxybenzyl)oxy]-2-[(2S)-oxiran-2-ylmethoxy]benzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

5-chloro-2-hydroxy-4-(4-methoxybenzyloxy)benzoic acid methyl ester (644971-05-1) + (2s)-(+)-glycidyl 3-nitrobenzenesulfonate (115314-14-2) → methyl 5-chloro-4-[(4-methoxybenzyl)oxy]-2-[(2S)-oxiran-2-ylmethoxy]benzoate (644971-06-2)

Guidance literature:

With caesium carbonate; In 1-methyl-pyrrolidin-2-one; at 20 ℃;

Reference yield:

p-methoxybenzyl chloride (824-94-2) → methyl 5-chloro-4-[(4-methoxybenzyl)oxy]-2-[(2S)-oxiran-2-ylmethoxy]benzoate (644971-06-2)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / acetone

2: caesium carbonate / N,N-dimethyl-formamide / 20 h / 20 °C

With potassium carbonate; caesium carbonate; In N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.bmcl.2013.04.047

Reference yield: 100.0%

methyl 5-chloro-4-[(4-methoxybenzyl)oxy]-2-[(2S)-oxiran-2-ylmethoxy]benzoate (644971-06-2) + 5-chloro-2,3-dihydrospiro (71916-97-7) → methyl 5-chloro-2-{[(2S)-3-(5-chloro-1'H,3H-spiro[1-benzofuran-2,4'-piperidin]-1'-yl)-2-hydroxypropyl]oxy}-4-[(4-methoxybenzyl)oxy]benzoate

Guidance literature:

In ethanol; Heating / reflux;

upstream raw materials:

5-chloro-2-hydroxy-4-(4-methoxybenzyloxy)benzoic acid methyl ester

(2s)-(+)-glycidyl 3-nitrobenzenesulfonate

p-methoxybenzyl chloride

Downstream raw materials:

methyl 5-chloro-2-{[(2S)-3-(5-chloro-1'H,3H-spiro[1-benzofuran-2,4'-piperidin]-1'-yl)-2-hydroxypropyl]oxy}-4-hydroxybenzoate trifluoroacetate

5-fluoro-2-{[(2S)-3-(5-chloro-1'H,3H-spiro[1-benzofuran-2,4'-piperidin]-1'-yl)-2-hydroxypropyl]oxy}-4-[(4-methoxybenzyl)oxy]benzoic acid hydrochloride

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