(S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-{2-[((S)-1-methoxycarbonyl-ethylamino)-methyl]-phenyl}-propionic acid 2-trimethylsilanyl-ethyl ester

Base Information

• Chemical Name: (S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-{2-[((S)-1-methoxycarbonyl-ethylamino)-methyl]-phenyl}-propionic acid 2-trimethylsilanyl-ethyl ester
• CAS No.: 177944-10-4
• Molecular Formula: C₂₇H₃₄N₂O₆Si
• Molecular Weight: 510.662
• Mol file: 177944-10-4.mol

Synonyms:

Chemical Property of (S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-{2-[((S)-1-methoxycarbonyl-ethylamino)-methyl]-phenyl}-propionic acid 2-trimethylsilanyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-{2-[((S)-1-methoxycarbonyl-ethylamino)-methyl]-phenyl}-propionic acid 2-trimethylsilanyl-ethyl ester

There total 10 articles about (S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-{2-[((S)-1-methoxycarbonyl-ethylamino)-methyl]-phenyl}-propionic acid 2-trimethylsilanyl-ethyl 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: 69.0%

L-alanine methyl ester hydrochloride (2491-20-5) + (S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-(2-formyl-phenyl)-propionic acid 2-trimethylsilanyl-ethyl ester (177944-09-1) → (S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-{2-[((S)-1-methoxycarbonyl-ethylamino)-methyl]-phenyl}-propionic acid 2-trimethylsilanyl-ethyl ester (177944-10-4)

Guidance literature:

With sodium cyanoborohydride;

DOI:10.1016/0960-894X(96)00149-7

Reference yield:

Homophthalic acid (89-51-0) → (S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-{2-[((S)-1-methoxycarbonyl-ethylamino)-methyl]-phenyl}-propionic acid 2-trimethylsilanyl-ethyl ester (177944-10-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 100 percent / LiAlH₄

2: 72 percent / LiCl, collidine / dimethylformamide

3: 82 percent / t-BuOK / diethyl ether / 0 °C

4: 96 percent / NaI / acetone

5: 1.) BuLi / 1.) HMPA

6: 100 percent / 1.) 0.5N HCl, 2.) LiOH

7: 73 percent / Na₂CO₃ / H₂O

8: 82 percent / EDC / pyridine

9: 85 percent / 1.) O₃, 2.) DMS

10: 69 percent / NaBH₃CN

With 2,3,5-trimethyl-pyridine; hydrogenchloride; lithium hydroxide; lithium aluminium tetrahydride; n-butyllithium; 2,3-dimercapto-succinic acid; potassium tert-butylate; sodium cyanoborohydride; sodium carbonate; ozone; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; sodium iodide; lithium chloride; In pyridine; diethyl ether; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/0960-894X(96)00149-7

Reference yield:

2-(2-hydroxyethyl)benzyl alcohol (6346-00-5) → (S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-{2-[((S)-1-methoxycarbonyl-ethylamino)-methyl]-phenyl}-propionic acid 2-trimethylsilanyl-ethyl ester (177944-10-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 72 percent / LiCl, collidine / dimethylformamide

2: 82 percent / t-BuOK / diethyl ether / 0 °C

3: 96 percent / NaI / acetone

4: 1.) BuLi / 1.) HMPA

5: 100 percent / 1.) 0.5N HCl, 2.) LiOH

6: 73 percent / Na₂CO₃ / H₂O

7: 82 percent / EDC / pyridine

8: 85 percent / 1.) O₃, 2.) DMS

9: 69 percent / NaBH₃CN

With 2,3,5-trimethyl-pyridine; hydrogenchloride; lithium hydroxide; n-butyllithium; 2,3-dimercapto-succinic acid; potassium tert-butylate; sodium cyanoborohydride; sodium carbonate; ozone; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; sodium iodide; lithium chloride; In pyridine; diethyl ether; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/0960-894X(96)00149-7

upstream raw materials:

L-alanine methyl ester hydrochloride

(S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-(2-formyl-phenyl)-propionic acid 2-trimethylsilanyl-ethyl ester

Homophthalic acid

2-(2-hydroxyethyl)benzyl alcohol