(S)-2-[N'-(3,4-Dimethoxy-2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionic acid cyanomethyl ester

Base Information

• Chemical Name: (S)-2-[N'-(3,4-Dimethoxy-2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionic acid cyanomethyl ester
• CAS No.: 205748-76-1
• Molecular Formula: C₂₁H₂₂N₄O₈
• Molecular Weight: 458.428
• Mol file: 205748-76-1.mol

Synonyms:(S)-2-[N'-(3,4-Dimethoxy-2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionic acid cyanomethyl ester

Chemical Property of (S)-2-[N'-(3,4-Dimethoxy-2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionic acid cyanomethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[N'-(3,4-Dimethoxy-2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionic acid cyanomethyl ester

There total 8 articles about (S)-2-[N'-(3,4-Dimethoxy-2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionic acid cyanomethyl 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: 71.0%

chloroacetonitrile (107-14-2) + (S)-2-[N'-(3,4-Dimethoxy-2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionic acid (205748-74-9) → (S)-2-[N'-(3,4-Dimethoxy-2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionic acid cyanomethyl ester (205748-76-1)

Guidance literature:

With triethylamine; In acetonitrile; at 25 ℃; for 15h;

DOI:10.1021/ja974066e

Reference yield:

D-phenyllactic acid (828-01-3,7326-19-4,20312-36-1,156-05-8) → (S)-2-[N'-(3,4-Dimethoxy-2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionic acid cyanomethyl ester (205748-76-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / tetrahydrofuran

2: 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

3: CH₂Cl₂ / 19 h / 0 - 20 °C

4: aq. CF₃CO₂H / CH₂Cl₂ / 2 h / 0 °C

5: 1N aq. NaOH / methanol / 2 h / 0 - 20 °C

6: 39 percent / aq. Na₂CO₃ / dioxane / 5 h / 25 °C

7: 71 percent / Et₃N / acetonitrile / 15 h / 25 °C

With 2,6-dimethylpyridine; sodium hydroxide; sodium carbonate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; acetonitrile;

DOI:10.1021/ja974066e

Reference yield:

(S)-2-hydrazinyl-3-phenylpropanoic acid (1202-31-9,13079-06-6) → (S)-2-[N'-(3,4-Dimethoxy-2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionic acid cyanomethyl ester (205748-76-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 39 percent / aq. Na₂CO₃ / dioxane / 5 h / 25 °C

2: 71 percent / Et₃N / acetonitrile / 15 h / 25 °C

With sodium carbonate; triethylamine; In 1,4-dioxane; acetonitrile;

DOI:10.1021/ja974066e

upstream raw materials:

chloroacetonitrile

(S)-2-[N'-(3,4-Dimethoxy-2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionic acid

D-phenyllactic acid

D-(R)-phenylalanine