(S)-2H-ISOINDOLE-2-ACETIC ACID, 1,3-DIHYDRO-ALPHA-[(4-METHOXYPHENYL)METHYL]-1,3-DIOXO-, METHYL ESTER

Base Information

• Chemical Name: (S)-2H-ISOINDOLE-2-ACETIC ACID, 1,3-DIHYDRO-ALPHA-[(4-METHOXYPHENYL)METHYL]-1,3-DIOXO-, METHYL ESTER
• CAS No.: 156624-78-1
• Molecular Formula: C₁₉H₁₇NO₅
• Molecular Weight: 339.348
• Mol file: 156624-78-1.mol

Synonyms:(S)-2H-ISOINDOLE-2-ACETIC ACID, 1,3-DIHYDRO-ALPHA-[(4-METHOXYPHENYL)METHYL]-1,3-DIOXO-, METHYL ESTER

Chemical Property of (S)-2H-ISOINDOLE-2-ACETIC ACID, 1,3-DIHYDRO-ALPHA-[(4-METHOXYPHENYL)METHYL]-1,3-DIOXO-, METHYL ESTER

Chemical Property:

• Boiling Point: 502.6±45.0 °C(Predicted)
• PKA: -2.51±0.20(Predicted)
• Density: 1.308±0.06 g/cm3(Predicted)

Purity/Quality:

(S)-1,3-DIHYDRO-ALPHA-[(4-METHOXYPHENYL)METHYL]-1,3-DIOXO-2H-ISOINDOLE-2-ACETIC ACID METHYL ESTER 95.00% ^*data from reagent suppliers

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Technology Process of (S)-2H-ISOINDOLE-2-ACETIC ACID, 1,3-DIHYDRO-ALPHA-[(4-METHOXYPHENYL)METHYL]-1,3-DIOXO-, METHYL ESTER

There total 8 articles about (S)-2H-ISOINDOLE-2-ACETIC ACID, 1,3-DIHYDRO-ALPHA-[(4-METHOXYPHENYL)METHYL]-1,3-DIOXO-, METHYL ESTER 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: 90.0%

methyl (S)-2-(1,3-dioxoisoindolin-2-yl)-3-(4-hydroxyphenyl)propanoate (39739-09-8) + dimethyl sulfate (77-78-1) → methyl (S)-2-(1,3-dioxoisoindolin-2-yl)-3-(4-methoxyphenyl)propanoate (156624-78-1)

Guidance literature:

With potassium carbonate; In acetone; Inert atmosphere; Reflux;

DOI:10.1021/jacs.7b10076

Reference yield: 72.0%

methanol (67-56-1) + (S)-N-(2-(dimethylamino)ethyl)-2-(1,3-dioxoisoindolin-2-yl)-3-(4-methoxyphenyl)propanamide → methyl (S)-2-(1,3-dioxoisoindolin-2-yl)-3-(4-methoxyphenyl)propanoate (156624-78-1)

Guidance literature:

With boron trifluoride diethyl etherate; at 110 ℃; for 20h;

DOI:10.1002/adsc.201801022

Reference yield:

methyl 2-phthalimidoacrylate (26878-24-0) + 4-methoxyphenylboronic acid (5720-07-0) → methyl (R)-2-(1,3-dioxoisoindolin-2-yl)-3-(4-methoxyphenyl)propanoate (1242459-50-2,156624-78-1) + methyl (S)-2-(1,3-dioxoisoindolin-2-yl)-3-(4-methoxyphenyl)propanoate (156624-78-1)

Guidance literature:

methyl 2-phthalimidoacrylate; 4-methoxyphenylboronic acid; With [RhCl(cis-cyclooctene)2]2; C₂₂H₁₆F₆; In toluene; at 20 ℃; for 0.5h; Inert atmosphere;

With water; potassium hydroxide; In toluene; at 80 ℃; for 8h; Overall yield = 99percent; enantioselective reaction; Inert atmosphere;

DOI:10.1039/d0ob00616e

upstream raw materials:

methyl 2-bromo-3-(4-methoxyphenyl)propanoate

potassium phtalimide

para-iodoanisole

Phth-L-Ala-OH

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