(R)-N⁴-Benzyloxy-N¹-[(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide

Base Information

• Chemical Name: (R)-N⁴-Benzyloxy-N¹-[(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide
• CAS No.: 171347-80-1
• Molecular Formula: C₂₇H₃₄N₄O₄
• Molecular Weight: 478.591

Synonyms:(R)-N⁴-Benzyloxy-N¹-[(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide

Chemical Property of (R)-N⁴-Benzyloxy-N¹-[(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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MSDS Files:

SDS file from LookChem

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Technology Process of (R)-N⁴-Benzyloxy-N¹-[(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide

There total 10 articles about (R)-N⁴-Benzyloxy-N¹-[(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide 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: 32.0%

benzyl bromide (100-39-0) + galardin (142880-36-2) → (R)-N4-Benzyloxy-N1-[(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide (171347-80-1)

Guidance literature:

With potassium carbonate; In methanol; for 24h; Ambient temperature;

DOI:10.1021/jm970494j

Reference yield:

2-methyl-2-propen-1-yl succinic anhydride (18908-20-8) → (R)-N4-Benzyloxy-N1-[(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide (171347-80-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 97.6 percent / H₂ / 10percent Pd/C / toluene / 14 h / 60 - 70 °C / 3102.9 Torr

2: 55.9 percent / 192 h / Ambient temperature

3: 64 percent / diethyl ether / 24 h / Ambient temperature

4: 98 percent / 1 N HCl / CHCl₃

5: 1.) CDI, 2.) Et₃N / 1.) THF, RT, 2 h, 2.) THF, RT

6: KOH, HONH₂*HCl / methanol / Ambient temperature

7: 32 percent / K₂CO₃ / methanol / 24 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; hydroxylamine hydrochloride; hydrogen; potassium carbonate; triethylamine; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In methanol; diethyl ether; chloroform; toluene;

DOI:10.1021/jm970494j

Reference yield:

Nα-Boc-L-tryptophan N-methylamide (122900-21-4) → (R)-N4-Benzyloxy-N1-[(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide (171347-80-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / 4 N HCl / dioxane; methanol / 4 h / Ambient temperature

2: 1.) CDI, 2.) Et₃N / 1.) THF, RT, 2 h, 2.) THF, RT

3: KOH, HONH₂*HCl / methanol / Ambient temperature

4: 32 percent / K₂CO₃ / methanol / 24 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; hydroxylamine hydrochloride; potassium carbonate; triethylamine; 1,1'-carbonyldiimidazole; In 1,4-dioxane; methanol;

DOI:10.1021/jm970494j

upstream raw materials:

benzyl bromide

galardin

2-methyl-2-propen-1-yl succinic anhydride

N^α-Boc-L-tryptophan N-methylamide

Downstream raw materials:

galardin

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