D-[2-(hydroxycabonyl)ethyl][3-(phenylacetyl)amino-3-(hydroxycarbonyl)propyl]phosphinic acid

Base Information

• Chemical Name: D-[2-(hydroxycabonyl)ethyl][3-(phenylacetyl)amino-3-(hydroxycarbonyl)propyl]phosphinic acid
• CAS No.: 352359-47-8
• Molecular Formula: C₁₅H₂₀NO₇P
• Molecular Weight: 357.3
• Mol file: 352359-47-8.mol

Synonyms:

Chemical Property of D-[2-(hydroxycabonyl)ethyl][3-(phenylacetyl)amino-3-(hydroxycarbonyl)propyl]phosphinic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of D-[2-(hydroxycabonyl)ethyl][3-(phenylacetyl)amino-3-(hydroxycarbonyl)propyl]phosphinic acid

There total 5 articles about D-[2-(hydroxycabonyl)ethyl][3-(phenylacetyl)amino-3-(hydroxycarbonyl)propyl]phosphinic acid 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:

ethyl [2-(ethoxycarbonyl)ethyl](vinyl)phosphinate (38056-67-6) → D-[2-(hydroxycabonyl)ethyl][3-(phenylacetyl)amino-3-(hydroxycarbonyl)propyl]phosphinic acid (352359-47-8)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate; tetrabutylammonium bromide / tetrahydrofuran / 13 h / Heating

2: 5.3 g / HCl; Dowex 50W (H⁽¹⁺⁾) / 15 h / Heating

3: 79 percent / KOH / dioxane; H₂O / 15 h / 20 °C / pH 9.5

4: immobilized penicillinamidase / H₂O / pH 7.5

With hydrogenchloride; potassium hydroxide; Dowex 50W (H⁽¹⁺⁾); immobilized penicillinamidase; tetrabutylammomium bromide; potassium carbonate; In tetrahydrofuran; 1,4-dioxane; water; 1: Michael addition / 3: Schotten-Baumann reaction;

DOI:10.1007/s11176-005-0133-1

Reference yield:

(2-bromoethyl)-[2-(ethoxycarbonyl)ethyl]phosphinic acid (856766-88-6) → D-[2-(hydroxycabonyl)ethyl][3-(phenylacetyl)amino-3-(hydroxycarbonyl)propyl]phosphinic acid (352359-47-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 3.8 g / 3 h / Heating

2: potassium carbonate; tetrabutylammonium bromide / tetrahydrofuran / 13 h / Heating

3: 5.3 g / HCl; Dowex 50W (H⁽¹⁺⁾) / 15 h / Heating

4: 79 percent / KOH / dioxane; H₂O / 15 h / 20 °C / pH 9.5

5: immobilized penicillinamidase / H₂O / pH 7.5

With hydrogenchloride; potassium hydroxide; Dowex 50W (H⁽¹⁺⁾); immobilized penicillinamidase; tetrabutylammomium bromide; potassium carbonate; In tetrahydrofuran; 1,4-dioxane; water; 2: Michael addition / 4: Schotten-Baumann reaction;

DOI:10.1007/s11176-005-0133-1

Reference yield:

(+/-)-PCEP (351904-41-1) → D-[2-(hydroxycabonyl)ethyl][3-(phenylacetyl)amino-3-(hydroxycarbonyl)propyl]phosphinic acid (352359-47-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / KOH / dioxane; H₂O / 15 h / 20 °C / pH 9.5

2: immobilized penicillinamidase / H₂O / pH 7.5

With potassium hydroxide; immobilized penicillinamidase; In 1,4-dioxane; water; 1: Schotten-Baumann reaction;

DOI:10.1007/s11176-005-0133-1

upstream raw materials:

[2-(hydroxycabonyl)ethyl][3-(phenylacetyl)amino-3-(hydroxycarbonyl)propyl]phosphinic acid

ethyl [2-(ethoxycarbonyl)ethyl](vinyl)phosphinate

(2-bromoethyl)-[2-(ethoxycarbonyl)ethyl]phosphinic acid

(+/-)-PCEP