(2E)-3-{4-[((benzyloxy)carbonyl)amino]phenyl}prop-2-enyl diazoacetate

Base Information

• Chemical Name: (2E)-3-{4-[((benzyloxy)carbonyl)amino]phenyl}prop-2-enyl diazoacetate
• CAS No.: 777089-59-5
• Molecular Formula: C₁₉H₁₇N₃O₄
• Molecular Weight: 351.362
• Mol file: 777089-59-5.mol

Synonyms:(2E)-3-{4-[((benzyloxy)carbonyl)amino]phenyl}prop-2-enyl diazoacetate

Chemical Property of (2E)-3-{4-[((benzyloxy)carbonyl)amino]phenyl}prop-2-enyl diazoacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E)-3-{4-[((benzyloxy)carbonyl)amino]phenyl}prop-2-enyl diazoacetate

There total 5 articles about (2E)-3-{4-[((benzyloxy)carbonyl)amino]phenyl}prop-2-enyl diazoacetate 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: 52.0%

benzyl 4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate (777089-58-4) + p-toluenesulfonylhydrazone glyoxylic acid chloride (14661-69-9) → (2E)-3-{4-[((benzyloxy)carbonyl)amino]phenyl}prop-2-enyl diazoacetate (777089-59-5)

Guidance literature:

benzyl 4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate; p-toluenesulfonylhydrazone glyoxylic acid chloride; With N,N-dimethyl-aniline; In dichloromethane; at 0 ℃; for 0.5h;

With triethylamine; In dichloromethane; at 0 ℃; for 2h;

Reference yield:

(E)-2-(2-benzenesulfonylhydrazide)acetic acid + benzyl 4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate (777089-58-4) → (2E)-3-{4-[((benzyloxy)carbonyl)amino]phenyl}prop-2-enyl diazoacetate (777089-59-5)

Guidance literature:

(E)-2-(2-benzenesulfonylhydrazide)acetic acid; With 1-chloro-1-(dimethylamino)-2-methyl-1-propene; In dichloromethane; at 23 ℃; for 0.666667h;

benzyl 4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate; With N,N-dimethyl-aniline; triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ol050730h

Reference yield:

methyl (2E)-3-(4-{[(benzyloxy)carbonyl]amino}phenyl)acrylate (777089-57-3) → (2E)-3-{4-[((benzyloxy)carbonyl)amino]phenyl}prop-2-enyl diazoacetate (777089-59-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 52 percent / LiAlH₄ / tetrahydrofuran / -78 - -20 °C

2.1: Me₂CH=C(Cl)NMe₂ / CH₂Cl₂ / 0.67 h / 23 °C

2.2: N,N-dimethylaniline; Et₃N / CH₂Cl₂ / 0 - 20 °C

With lithium aluminium tetrahydride; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol050730h

upstream raw materials:

benzyl 4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate

methyl (2E)-3-(4-{[(benzyloxy)carbonyl]amino}phenyl)acrylate

benzyl N-(4-formylphenyl)carbamate

benzyl (4-bromophenyl)carbamate

Downstream raw materials:

Methanesulfonic acid (1S,2S,3R)-2-(4-benzyloxycarbonylamino-phenyl)-3-methanesulfonyloxymethyl-cyclopropylmethyl ester

{4-[(1S,5R,6S)-3-(4-Methoxy-benzyl)-3-aza-bicyclo[3.1.0]hex-6-yl]-phenyl}-carbamic acid benzyl ester

[4-((1S,2R,3S)-2,3-Bis-hydroxymethyl-cyclopropyl)-phenyl]-carbamic acid benzyl ester

[(1S,5R,6S)-4-(3-Thia-bicyclo[3.1.0]hex-6-yl)-phenyl]-carbamic acid benzyl ester

Refernces

• 1、 -. "ANTIMICROBIAL [3.1.0] BICYCLOHEXYLPHENYL-OXAZOLIDINONE DERIVATIVES AND ANALOGUES". Page 86-87. . Retrieved 2010/02/09.