[(S)-1-Benzyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-thioxo-ethyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(S)-1-Benzyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-thioxo-ethyl]-carbamic acid tert-butyl ester
• CAS No.: 191405-19-3
• Molecular Formula: C₂₂H₂₂N₂O₄S
• Molecular Weight: 410.494

Synonyms:[(S)-1-Benzyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-thioxo-ethyl]-carbamic acid tert-butyl ester

Chemical Property of [(S)-1-Benzyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-thioxo-ethyl]-carbamic acid tert-butyl ester

Chemical Property:

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Technology Process of [(S)-1-Benzyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-thioxo-ethyl]-carbamic acid tert-butyl ester

There total 2 articles about [(S)-1-Benzyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-thioxo-ethyl]-carbamic acid tert-butyl 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: 65.0%

tert-butyl [(2S)-1-amino-3-phenyl-1-thioxopropan-2-yl]carbamate (99281-95-5) + Phthaloyl dichloride (88-95-9) → [(S)-1-Benzyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-thioxo-ethyl]-carbamic acid tert-butyl ester (191405-19-3)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/jo970528v

Reference yield:

(S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide (88463-18-7,35150-06-2) → [(S)-1-Benzyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-thioxo-ethyl]-carbamic acid tert-butyl ester (191405-19-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / Lawesson's reagent / tetrahydrofuran / Ambient temperature

2: 65 percent / K₂CO₃ / tetrahydrofuran / 0 °C

With Lawessons reagent; potassium carbonate; In tetrahydrofuran;

DOI:10.1021/jo970528v

Reference yield: 98.0%

(S)-2-amino-N-benzylpropanamide (75040-72-1) + [(S)-1-Benzyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-thioxo-ethyl]-carbamic acid tert-butyl ester (191405-19-3) → [(S)-1-((S)-1-Benzylcarbamoyl-ethylthiocarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

Guidance literature:

In chloroform; at 0 ℃; for 0.166667h;

DOI:10.1021/jo970528v

upstream raw materials:

tert-butyl [(2S)-1-amino-3-phenyl-1-thioxopropan-2-yl]carbamate

Phthaloyl dichloride

(S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide

Downstream raw materials:

5-(S)-benzyl-3-[(S)-1-[N-(tert-butoxycarbonyl)amino]-2-phenethyl]-4,5-dihydro-1,2,4-triazin-6-(1H)-one

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