N-CBZ-β-benzyl-L-aspartyl-D-α-aminopentanoic acid (S)-α-methylbenzylamide

Base Information

• Chemical Name: N-CBZ-β-benzyl-L-aspartyl-D-α-aminopentanoic acid (S)-α-methylbenzylamide
• CAS No.: 165055-12-9
• Molecular Formula: C₃₂H₃₇N₃O₆
• Molecular Weight: 559.662

Synonyms:N-CBZ-β-benzyl-L-aspartyl-D-α-aminopentanoic acid (S)-α-methylbenzylamide

Chemical Property of N-CBZ-β-benzyl-L-aspartyl-D-α-aminopentanoic acid (S)-α-methylbenzylamide

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Technology Process of N-CBZ-β-benzyl-L-aspartyl-D-α-aminopentanoic acid (S)-α-methylbenzylamide

There total 3 articles about N-CBZ-β-benzyl-L-aspartyl-D-α-aminopentanoic acid (S)-α-methylbenzylamide 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%

(S)-1-phenyl-ethylamine (2627-86-3) + N-(carbobenzyloxy)-β-benzyl-L-aspartyl-D-α-aminopentanoic acid (154653-23-3) → N-CBZ-β-benzyl-L-aspartyl-D-α-aminopentanoic acid (S)-α-methylbenzylamide (165055-12-9)

Guidance literature:

With N-hydroxy-5-norbornene-2,3-dicarboximide; dicyclohexyl-carbodiimide; In 1,4-dioxane; Ambient temperature;

DOI:10.1021/jf00056a003

Reference yield:

Z-Asp(OBzl)-OH (3479-47-8) → N-CBZ-β-benzyl-L-aspartyl-D-α-aminopentanoic acid (S)-α-methylbenzylamide (165055-12-9)

Guidance literature:

Multi-step reaction with 3 steps

1: dicyclohexylcarbodiimide / tetrahydrofuran / Ambient temperature

2: 73 percent / Et₃N / dioxane; H₂O / Ambient temperature

3: 69 percent / dicyclohexylcarbodiimide, N-hydroxy-5-norbornene-2,3-dicarboximide / dioxane / Ambient temperature

With N-hydroxy-5-norbornene-2,3-dicarboximide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1021/jf00056a003

Reference yield:

Oγ-benzyl-Nα-benzyloxycarbonylaspartic acid succinimidyl ester (61464-33-3) → N-CBZ-β-benzyl-L-aspartyl-D-α-aminopentanoic acid (S)-α-methylbenzylamide (165055-12-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / Et₃N / dioxane; H₂O / Ambient temperature

2: 69 percent / dicyclohexylcarbodiimide, N-hydroxy-5-norbornene-2,3-dicarboximide / dioxane / Ambient temperature

With N-hydroxy-5-norbornene-2,3-dicarboximide; triethylamine; dicyclohexyl-carbodiimide; In 1,4-dioxane; water;

DOI:10.1021/jf00056a003

upstream raw materials:

(S)-1-phenyl-ethylamine

N-(carbobenzyloxy)-β-benzyl-L-aspartyl-D-α-aminopentanoic acid

Z-Asp(OBzl)-OH

O^γ-benzyl-N^α-benzyloxycarbonylaspartic acid succinimidyl ester

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