5-(3-{4-[(3-acetyl-phenoxy)-ethyl-phosphinoyloxy]-phenyl}-3-hydroxy-propionylamino)-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester

Base Information

• Chemical Name: 5-(3-{4-[(3-acetyl-phenoxy)-ethyl-phosphinoyloxy]-phenyl}-3-hydroxy-propionylamino)-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester
• CAS No.: 405196-22-7
• Molecular Formula: C₂₈H₃₃N₂O₁₀P
• Molecular Weight: 588.551
• Mol file: 405196-22-7.mol

Synonyms:5-(3-{4-[(3-acetyl-phenoxy)-ethyl-phosphinoyloxy]-phenyl}-3-hydroxy-propionylamino)-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester

Chemical Property of 5-(3-{4-[(3-acetyl-phenoxy)-ethyl-phosphinoyloxy]-phenyl}-3-hydroxy-propionylamino)-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(3-{4-[(3-acetyl-phenoxy)-ethyl-phosphinoyloxy]-phenyl}-3-hydroxy-propionylamino)-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester

There total 9 articles about 5-(3-{4-[(3-acetyl-phenoxy)-ethyl-phosphinoyloxy]-phenyl}-3-hydroxy-propionylamino)-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl 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%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 5-(3-{4-[(3-acetyl-phenoxy)ethyl-phosphinoyloxy]phenyl}-3-hydroxy-propionylamino)pentanoic acid (405196-21-6) → 5-(3-{4-[(3-acetyl-phenoxy)-ethyl-phosphinoyloxy]-phenyl}-3-hydroxy-propionylamino)-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester (405196-22-7)

Guidance literature:

With dicyclohexyl-carbodiimide; In 1,4-dioxane; at 20 ℃; for 16h;

DOI:10.1016/S0968-0896(01)00231-0

Reference yield:

3-Hydroxyacetophenone (121-71-1) → 5-(3-{4-[(3-acetyl-phenoxy)-ethyl-phosphinoyloxy]-phenyl}-3-hydroxy-propionylamino)-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester (405196-22-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 50 percent / diisopropylethylamine / CH₂Cl₂ / 3 h / 20 °C

2: 99 percent / hydrogen / Pd/C / ethyl acetate / 0.67 h

3: 90 percent / 1,3-dicyclohexylcarbodiimide / dioxane / 16 h / 20 °C

With hydrogen; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 1,4-dioxane; dichloromethane; ethyl acetate;

DOI:10.1016/S0968-0896(01)00231-0

Reference yield:

4-(trimethylsiloxy)benzaldehyde (1012-12-0) → 5-(3-{4-[(3-acetyl-phenoxy)-ethyl-phosphinoyloxy]-phenyl}-3-hydroxy-propionylamino)-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester (405196-22-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 3 h / -78 °C

2.1: TFA / acetonitrile; methanol / 12 h / 20 °C

2.2: 5.06 g / hydrogen / Pd/C / ethanol / 3 h / 760 Torr

3.1: 55 percent / (3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole monohydrate; diisopropylethylamine / dimethylformamide / 24 h / 20 °C

4.1: 50 percent / diisopropylethylamine / CH₂Cl₂ / 3 h / 20 °C

5.1: 99 percent / hydrogen / Pd/C / ethyl acetate / 0.67 h

6.1: 90 percent / 1,3-dicyclohexylcarbodiimide / dioxane / 16 h / 20 °C

With n-butyllithium; hydrogen; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diisopropylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0968-0896(01)00231-0

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

5-(3-{4-[(3-acetyl-phenoxy)ethyl-phosphinoyloxy]phenyl}-3-hydroxy-propionylamino)pentanoic acid

3-Hydroxyacetophenone

4-(trimethylsiloxy)benzaldehyde