S-[(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl] ethanethioate

Base Information

• Chemical Name: S-[(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl] ethanethioate
• CAS No.: 856421-78-8
• Molecular Formula: C₁₉H₁₇NO₃S
• Molecular Weight: 339.415
• Mol file: 856421-78-8.mol

Synonyms:S-[(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl] ethanethioate

Chemical Property of S-[(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl] ethanethioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of S-[(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl] ethanethioate

There total 4 articles about S-[(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl] ethanethioate 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: 80.0%

(2R)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl methanesulfonate (74397-33-4) + tiolacetic acid (507-09-5) → S-[(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl] ethanethioate (856421-78-8)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 24h;

DOI:10.1016/j.tetlet.2005.04.011

Reference yield:

(R)-2-amino-3-phenylpropanol (5267-64-1) → S-[(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl] ethanethioate (856421-78-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / 140 °C

2: 84 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

3: 80 percent / Cs₂CO₃ / dimethylformamide / 24 h / 50 °C

With caesium carbonate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2005.04.011

Reference yield:

D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) → S-[(2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl] ethanethioate (856421-78-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaBH₄; I₂ / tetrahydrofuran / Heating

1.2: MeOH

2.1: 96 percent / 140 °C

3.1: 84 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

4.1: 80 percent / Cs₂CO₃ / dimethylformamide / 24 h / 50 °C

With sodium tetrahydroborate; iodine; caesium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2005.04.011

upstream raw materials:

(2R)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl methanesulfonate

tiolacetic acid

(R)-2-amino-3-phenylpropanol

D-(R)-phenylalanine