(S)-3-(3-Chloro-4-hydroxy-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester

Base Information

• Chemical Name: (S)-3-(3-Chloro-4-hydroxy-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester
• CAS No.: 159526-60-0
• Molecular Formula: C₁₈H₁₄ClNO₅
• Molecular Weight: 359.766
• Mol file: 159526-60-0.mol

Synonyms:(S)-3-(3-Chloro-4-hydroxy-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester

Chemical Property of (S)-3-(3-Chloro-4-hydroxy-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-(3-Chloro-4-hydroxy-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester

There total 4 articles about (S)-3-(3-Chloro-4-hydroxy-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid 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: 94.0%

methyl (S)-2-(1,3-dioxoisoindolin-2-yl)-3-(4-hydroxyphenyl)propanoate (39739-09-8) → (S)-3-(3-Chloro-4-hydroxy-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester (159526-60-0)

Guidance literature:

With sulfuryl dichloride; In diethyl ether; for 0.25h; Ambient temperature;

DOI:10.1016/S0040-4039(00)73315-6

Reference yield:

N-ethoxycarbonylphthalimide (22509-74-6) → (S)-3-(3-Chloro-4-hydroxy-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester (159526-60-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / NaOH / 0.5 h / 0 °C

2: 83 percent / H₂SO₄ / 6 h / Heating

3: 94 percent / SO₂Cl₂ / diethyl ether / 0.25 h / Ambient temperature

With sodium hydroxide; sulfuryl dichloride; sulfuric acid; In diethyl ether;

DOI:10.1016/S0040-4039(00)73315-6

Reference yield:

N-phthaloyl-L-tyrosine (29588-94-1,6319-55-7) → (S)-3-(3-Chloro-4-hydroxy-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester (159526-60-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / H₂SO₄ / 6 h / Heating

2: 94 percent / SO₂Cl₂ / diethyl ether / 0.25 h / Ambient temperature

With sulfuryl dichloride; sulfuric acid; In diethyl ether;

DOI:10.1016/S0040-4039(00)73315-6

upstream raw materials:

methyl (S)-2-(1,3-dioxoisoindolin-2-yl)-3-(4-hydroxyphenyl)propanoate

N-ethoxycarbonylphthalimide

N-phthaloyl-L-tyrosine

L-tyrosine

Downstream raw materials:

(2S,3R)-3-(4-Acetoxy-3-chloro-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester

(2S,3R)-methyl 2-phthalimido-3-(^tbutyldimethylsilyloxy)-3-(3'-chloro-4'-hydroxy phenyl)propionate

(R)-3-(4-Acetoxy-3-chloro-phenyl)-3-bromo-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester

(S)-3-(4-Acetoxy-3-chloro-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester