(R)-N-<2-(benzyloxycarbonyl)-1-oxoethyl>phenylalanine N'-(benzyloxy)-N'-methylamide

Base Information

• Chemical Name: (R)-N-<2-(benzyloxycarbonyl)-1-oxoethyl>phenylalanine N'-(benzyloxy)-N'-methylamide
• CAS No.: 115364-63-1
• Molecular Formula: C₂₇H₂₈N₂O₅
• Molecular Weight: 460.53

Synonyms:(R)-N-<2-(benzyloxycarbonyl)-1-oxoethyl>phenylalanine N'-(benzyloxy)-N'-methylamide

Chemical Property of (R)-N-<2-(benzyloxycarbonyl)-1-oxoethyl>phenylalanine N'-(benzyloxy)-N'-methylamide

Chemical Property:

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Technology Process of (R)-N-<2-(benzyloxycarbonyl)-1-oxoethyl>phenylalanine N'-(benzyloxy)-N'-methylamide

There total 4 articles about (R)-N-<2-(benzyloxycarbonyl)-1-oxoethyl>phenylalanine N'-(benzyloxy)-N'-methylamide 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: 20.5%

malonic acid monobenzyl ester (40204-26-0) + (R)-phenylalanine N'-(benzyloxy)-N'-methylamide trifluoroacetate (115364-62-0) → (R)-N-<2-(benzyloxycarbonyl)-1-oxoethyl>phenylalanine N'-(benzyloxy)-N'-methylamide (115364-63-1)

Guidance literature:

With 1-hydroxybenzotriazol-hydrate; triethylamine; dicyclohexyl-carbodiimide; In chloroform; 1.) 0 deg C, 1 h, 2.) room temperature, overnight;

DOI:10.1021/jm00117a025

Reference yield:

N-methyl-O-benzylhydroxylamine (22513-22-0) → (R)-N-<2-(benzyloxycarbonyl)-1-oxoethyl>phenylalanine N'-(benzyloxy)-N'-methylamide (115364-63-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 76.2 percent / triethylamine, 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide / CHCl₃ / 1.) 0 deg C, 1 h, 2.) room temperature, overnight

2: 86 percent / CH₂Cl₂ / 1 h / 0 °C

3: 20.5 percent / triethylamine, 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide / CHCl₃ / 1.) 0 deg C, 1 h, 2.) room temperature, overnight

With 1-hydroxybenzotriazol-hydrate; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; chloroform;

DOI:10.1021/jm00117a025

Reference yield:

Boc-D-Phe-OH (18942-49-9) → (R)-N-<2-(benzyloxycarbonyl)-1-oxoethyl>phenylalanine N'-(benzyloxy)-N'-methylamide (115364-63-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 76.2 percent / triethylamine, 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide / CHCl₃ / 1.) 0 deg C, 1 h, 2.) room temperature, overnight

2: 86 percent / CH₂Cl₂ / 1 h / 0 °C

3: 20.5 percent / triethylamine, 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide / CHCl₃ / 1.) 0 deg C, 1 h, 2.) room temperature, overnight

With 1-hydroxybenzotriazol-hydrate; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; chloroform;

DOI:10.1021/jm00117a025

upstream raw materials:

malonic acid monobenzyl ester

(R)-phenylalanine N'-(benzyloxy)-N'-methylamide trifluoroacetate

N-methyl-O-benzylhydroxylamine

Boc-D-Phe-OH

Downstream raw materials:

(R)-N-(2-carboxy-1-oxoethyl)phenylalanine N'-(benzyloxy)-N'-methylamide

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