(Benzyloxycarbonyl)-β-homo-L-aspartyl-L-phenylalaninamide β-tert-butyl ester

Base Information

• Chemical Name: (Benzyloxycarbonyl)-β-homo-L-aspartyl-L-phenylalaninamide β-tert-butyl ester
• CAS No.: 118247-83-9
• Molecular Formula: C₂₆H₃₃N₃O₆
• Molecular Weight: 483.565

Synonyms:(Benzyloxycarbonyl)-β-homo-L-aspartyl-L-phenylalaninamide β-tert-butyl ester

Chemical Property of (Benzyloxycarbonyl)-β-homo-L-aspartyl-L-phenylalaninamide β-tert-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (Benzyloxycarbonyl)-β-homo-L-aspartyl-L-phenylalaninamide β-tert-butyl ester

There total 5 articles about (Benzyloxycarbonyl)-β-homo-L-aspartyl-L-phenylalaninamide β-tert-butyl 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: 75.0%

L-Phenylalanine amide (5241-58-7) + (Benzyloxycarbonyl)-β-homo-L-aspartic acid α-pentachlorophenyl ester β-tert-butyl ester (118247-80-6) → (Benzyloxycarbonyl)-β-homo-L-aspartyl-L-phenylalaninamide β-tert-butyl ester (118247-83-9)

Guidance literature:

In N,N-dimethyl-formamide; for 3h; Ambient temperature;

DOI:10.1021/jm00123a003

Reference yield:

Z-D(tBu)-OH (5545-52-8) → (Benzyloxycarbonyl)-β-homo-L-aspartyl-L-phenylalaninamide β-tert-butyl ester (118247-83-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) isobutyl chloroformate, N-methylmorpholine / 1.) DME, -20 deg C, 5 min, 2.) DME, ether, 0 deg C, 20 min

2: silver benzoate, triethylamine / 30 h / Ambient temperature

3: 2 N NaOH / methanol / 0.5 h / 30 °C

4: 72 percent / dicyclohexylcarbodiimide / CH₂Cl₂ / 2 h / 0 °C

5: 75 percent / dimethylformamide / 3 h / Ambient temperature

With 4-methyl-morpholine; sodium hydroxide; silver benzoate; triethylamine; dicyclohexyl-carbodiimide; isobutyl chloroformate; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00123a003

Reference yield:

(3R)-3-benzyloxycarbonylamino-4-tert-butyoxycarbonylbutyric acid (83436-45-7) → (Benzyloxycarbonyl)-β-homo-L-aspartyl-L-phenylalaninamide β-tert-butyl ester (118247-83-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / dicyclohexylcarbodiimide / CH₂Cl₂ / 2 h / 0 °C

2: 75 percent / dimethylformamide / 3 h / Ambient temperature

With dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00123a003

upstream raw materials:

L-Phenylalanine amide

(Benzyloxycarbonyl)-β-homo-L-aspartic acid α-pentachlorophenyl ester β-tert-butyl ester

Z-D(tBu)-OH

(3R)-3-benzyloxycarbonylamino-4-tert-butyoxycarbonylbutyric acid

Downstream raw materials:

(tert-Butoxycarbonyl)-L-tryptophyl-L-leucyl-β-homo-L-aspartyl-L-phenylalaninamide

(R)-3-((S)-2-Amino-4-methyl-pentanoylamino)-4-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-butyric acid; compound with trifluoro-acetic acid

(tert-Butoxycarbonyl)-L-leucyl-β-homo-L-aspartyl-L-phenylalaninamide

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