(Z)-tert-butyl 2-(1-(4-(Methoxycarbonyl)phenyl)ethylidene)hydrazinecarboxylate

Base Information

• Chemical Name: (Z)-tert-butyl 2-(1-(4-(Methoxycarbonyl)phenyl)ethylidene)hydrazinecarboxylate
• CAS No.: 870822-87-0
• Molecular Formula: C16H22N2O4
• Molecular Weight: 306.362
• Mol file: 870822-87-0.mol

Synonyms:

Chemical Property of (Z)-tert-butyl 2-(1-(4-(Methoxycarbonyl)phenyl)ethylidene)hydrazinecarboxylate

Chemical Property:

• PSA: 80.48000
• LogP: 2.92630

Purity/Quality:

≥95% ^*data from raw suppliers

(Z)-tert-butyl2-(1-(4-(methoxycarbonyl)phenyl)ethylidene)hydrazinecarboxylate 95.32% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-tert-butyl 2-(1-(4-(Methoxycarbonyl)phenyl)ethylidene)hydrazinecarboxylate

There total 2 articles about (Z)-tert-butyl 2-(1-(4-(Methoxycarbonyl)phenyl)ethylidene)hydrazinecarboxylate 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: 94.2%

t-butoxycarbonylhydrazine (870-46-2) + ethyl-4-acetylbenzoate (38430-55-6) → tert-butyl N'-[1-[4-(ethoxycarbonyl)phenyl]ethylidene]hydrazinecarboxylate (870822-87-0)

Guidance literature:

With acetic acid; In toluene; at 58 - 62 ℃; for 3.5h; Inert atmosphere;

DOI:10.1021/ol902602c

Reference yield:

4-acetyl-benzoic acid (586-89-0) → tert-butyl N'-[1-[4-(ethoxycarbonyl)phenyl]ethylidene]hydrazinecarboxylate (870822-87-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / 3 h / 80 °C

2: acetic acid / toluene / 80 °C

With sulfuric acid; acetic acid; In toluene;

DOI:10.1016/j.bmc.2016.04.053

Reference yield: 98.0%

tert-butyl N'-[1-[4-(ethoxycarbonyl)phenyl]ethylidene]hydrazinecarboxylate (870822-87-0) → tert-butyl 2-{1-[4-(ethoxycarbonyl)phenyl]ethyl}hydrazin-1-carboxylate (870822-88-1)

Guidance literature:

With sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; Inert atmosphere;

DOI:10.1021/jm300579z

upstream raw materials:

t-butoxycarbonylhydrazine

ethyl-4-acetylbenzoate

4-acetyl-benzoic acid

Downstream raw materials:

tert-butyl 2-{1-[4-(ethoxycarbonyl)phenyl]ethyl}hydrazin-1-carboxylate

tert-butyl 2-{(1S)-1-[4-(ethoxycarbonyl)phenyl]ethyl}hydrazinecarboxylate

tert-butyl 2-{(1R)-1-[4-(ethoxycarbonyl)phenyl]ethyl}hydrazinecarboxylate

C₁₁H₁₆N₂O₂

Refernces

• 1、 Shu, Shuangjie,Cai, Xiaoqing,Li, Jia,Feng, Yang,Dai, Antao,Wang, Jiang,Yang, Dehua,Wang, Ming-Wei,Liu, Hong. "Design, synthesis, structure-activity relationships, and docking studies of pyrazole-containing derivatives as a novel series of potent glucagon receptor antagonists". . p. 2852 - 2863. Retrieved 2016/06/08.
• 2、 Yoshikawap, Naoki,Tan, Lushi,Christopher McWilliams,Ramasamy, Deepa,Sheppard, Ruth. "Catalytic enantioselective hydrogenation of N-alkoxycarbonyl hydrazones: A practical synthesis of chiral hydrazines". supporting information; experimental part. p. 276 - 279. Retrieved 2010/03/25.