3-1-(acetyl-L-leucyl-L-alanyl-β-alanyl)-N²-(benzyloxycarbonyl)hydrazino>-N,N-(dimethyl)propanamide

Base Information

• Chemical Name: 3-1-(acetyl-L-leucyl-L-alanyl-β-alanyl)-N²-(benzyloxycarbonyl)hydrazino>-N,N-(dimethyl)propanamide
• CAS No.: 227289-33-0
• Molecular Formula: C₂₇H₄₂N₆O₇
• Molecular Weight: 562.666

Synonyms:

Chemical Property of 3-1-(acetyl-L-leucyl-L-alanyl-β-alanyl)-N²-(benzyloxycarbonyl)hydrazino>-N,N-(dimethyl)propanamide

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of 3-1-(acetyl-L-leucyl-L-alanyl-β-alanyl)-N²-(benzyloxycarbonyl)hydrazino>-N,N-(dimethyl)propanamide

There total 7 articles about 3-1-(acetyl-L-leucyl-L-alanyl-β-alanyl)-N²-(benzyloxycarbonyl)hydrazino>-N,N-(dimethyl)propanamide 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:

N,N-Dimethylacrylamide (2680-03-7,68761-83-1) → 3-1-(acetyl-L-leucyl-L-alanyl-β-alanyl)-N2-(benzyloxycarbonyl)hydrazino>-N,N-(dimethyl)propanamide (227289-33-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 6.5 g / hydrazine monohydrate / methanol / 2 h / Ambient temperature

2: 53 percent / aq. NaOH / dioxane / 1 h / Ambient temperature

3: 87 percent / K₂CO₃ / tetrahydrofuran / 2 h / 40 - 50 °C

4: 1.) CF₃CO₂H, 2.) Et₃N / 1) CH₂Cl₂, rt, 2 h; 2) THF

5: 1.) Et₃N, ethyl chloroformate / 1) THF, -5 deg C, 20 min; 2) THF, -5 deg C, 30 min, rt, 2 h

6: 1.) CF₃CO₂H, 2.) Et₃N / 1) CH₂Cl₂, rt, 2 h; 2) THF

7: 1.) Et₃N, ethyl chloroformate / 1) THF, -5 deg C, 20 min; 2) THF, -5 deg C, 30 min, rt, 2 h

With sodium hydroxide; chloroformic acid ethyl ester; potassium carbonate; hydrazine hydrate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; methanol;

DOI:10.1016/S0968-0896(99)00006-1

Reference yield:

3-hydrazino-N,N-(dimethyl)propanamide (107746-30-5) → 3-1-(acetyl-L-leucyl-L-alanyl-β-alanyl)-N2-(benzyloxycarbonyl)hydrazino>-N,N-(dimethyl)propanamide (227289-33-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 53 percent / aq. NaOH / dioxane / 1 h / Ambient temperature

2: 87 percent / K₂CO₃ / tetrahydrofuran / 2 h / 40 - 50 °C

3: 1.) CF₃CO₂H, 2.) Et₃N / 1) CH₂Cl₂, rt, 2 h; 2) THF

4: 1.) Et₃N, ethyl chloroformate / 1) THF, -5 deg C, 20 min; 2) THF, -5 deg C, 30 min, rt, 2 h

5: 1.) CF₃CO₂H, 2.) Et₃N / 1) CH₂Cl₂, rt, 2 h; 2) THF

6: 1.) Et₃N, ethyl chloroformate / 1) THF, -5 deg C, 20 min; 2) THF, -5 deg C, 30 min, rt, 2 h

With sodium hydroxide; chloroformic acid ethyl ester; potassium carbonate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1016/S0968-0896(99)00006-1

Reference yield:

3-1-(tert-butoxycarbony)hydrazino>-N,N-(dimethyl)propanamide (227289-25-0) → 3-1-(acetyl-L-leucyl-L-alanyl-β-alanyl)-N2-(benzyloxycarbonyl)hydrazino>-N,N-(dimethyl)propanamide (227289-33-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / K₂CO₃ / tetrahydrofuran / 2 h / 40 - 50 °C

2: 1.) CF₃CO₂H, 2.) Et₃N / 1) CH₂Cl₂, rt, 2 h; 2) THF

3: 1.) Et₃N, ethyl chloroformate / 1) THF, -5 deg C, 20 min; 2) THF, -5 deg C, 30 min, rt, 2 h

4: 1.) CF₃CO₂H, 2.) Et₃N / 1) CH₂Cl₂, rt, 2 h; 2) THF

5: 1.) Et₃N, ethyl chloroformate / 1) THF, -5 deg C, 20 min; 2) THF, -5 deg C, 30 min, rt, 2 h

With chloroformic acid ethyl ester; potassium carbonate; triethylamine; trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1016/S0968-0896(99)00006-1

upstream raw materials:

Ac-Leu-Ala-OH

N,N-Dimethylacrylamide

3-hydrazino-N,N-(dimethyl)propanamide

3-1-(tert-butoxycarbony)hydrazino>-N,N-(dimethyl)propanamide

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