C^α-methyl-D,L-aspartic acid α-benzyl β-methyl diester

Base Information

• Chemical Name: C^α-methyl-D,L-aspartic acid α-benzyl β-methyl diester
• CAS No.: 155567-92-3
• Molecular Formula: C₁₃H₁₇NO₄
• Molecular Weight: 251.282
• Mol file: 155567-92-3.mol

Synonyms:C^α-methyl-D,L-aspartic acid α-benzyl β-methyl diester

Chemical Property of C^α-methyl-D,L-aspartic acid α-benzyl β-methyl diester

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of C^α-methyl-D,L-aspartic acid α-benzyl β-methyl diester

There total 1 articles about C^α-methyl-D,L-aspartic acid α-benzyl β-methyl diester 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:

bromoacetic acid methyl ester (96-32-2) + L-alanine benzyl ester benzophenone imine (143428-44-8) → Cα-methyl-D,L-aspartic acid α-benzyl β-methyl diester (155567-92-3)

Guidance literature:

With hydrogenchloride; potassium hexamethylsilazane; Yield given. Multistep reaction;

DOI:10.1021/ja00087a007

Reference yield: 98.0%

di-tert-butyl dicarbonate (24424-99-5) + Cα-methyl-D,L-aspartic acid α-benzyl β-methyl diester (155567-92-3) → Nα-(tert-butyloxycarbonyl)-Cα-methyl-D,L-aspartic acid α-benzyl β-methyl diester (155567-93-4)

Guidance literature:

With triethylamine; In tert-butyl alcohol; at 80 ℃; for 2h;

DOI:10.1021/ja00087a007

Reference yield:

Cα-methyl-D,L-aspartic acid α-benzyl β-methyl diester (155567-92-3) → Nα-(tert-butyloxycarbonyl)-Cα-methyl-D,L-aspartic acid β-cyclohexyl ester (155567-91-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / Et₃N / 2-methyl-propan-2-ol / 2 h / 80 °C

2: 47 percent / 25percent aq. NaOH / tetrahydrofuran; dioxane / 2.5 h

3: 93 percent / DMAP, DCC / CH₂Cl₂ / 1.5 h

4: 84 percent / H₂, AcOH / 10percent Pd/C / ethanol / 4 h / 2327.2 Torr

With dmap; sodium hydroxide; hydrogen; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; tert-butyl alcohol;

DOI:10.1021/ja00087a007

upstream raw materials:

bromoacetic acid methyl ester

L-alanine benzyl ester benzophenone imine

Downstream raw materials:

N^α-(tert-butyloxycarbonyl)-C^α-methyl-D,L-aspartic acid α-benzyl β-methyl diester

N^α-(tert-butyloxycarbonyl)-C^α-methyl-D,L-aspartic acid β-cyclohexyl ester

N^α-(tert-butyloxycarbonyl)-C^α-methyl-D,L-aspartic acid α-benzyl ester

N^α-(tert-butyloxycarbonyl)-C^α-methyl-D,L-aspartic acid α-benzyl β-cyclohexyl diester

Refernces