(2E)-3-{2,6-difluoro-4-[(benzyloxycarbonyl)amino]phenyl}prop-2-enyl diazoacetate

Base Information

Chemical Name:(2E)-3-{2,6-difluoro-4-[(benzyloxycarbonyl)amino]phenyl}prop-2-enyl diazoacetate
CAS No.:777089-86-8
Molecular Formula:C₁₉H₁₅F₂N₃O₄
Molecular Weight:387.343
Hs Code.:

Synonyms:(2E)-3-{2,6-difluoro-4-[(benzyloxycarbonyl)amino]phenyl}prop-2-enyl diazoacetate

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Chemical Property of (2E)-3-{2,6-difluoro-4-[(benzyloxycarbonyl)amino]phenyl}prop-2-enyl diazoacetate

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Technology Process of (2E)-3-{2,6-difluoro-4-[(benzyloxycarbonyl)amino]phenyl}prop-2-enyl diazoacetate

There total 7 articles about (2E)-3-{2,6-difluoro-4-[(benzyloxycarbonyl)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: 80.0%

: benzyl 2,6-difluoro-4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate

: 14661-69-9
p-toluenesulfonylhydrazone glyoxylic acid chloride

: 777089-86-8
(2E)-3-{2,6-difluoro-4-[(benzyloxycarbonyl)amino]phenyl}prop-2-enyl diazoacetate

Guidance literature:: p-toluenesulfonylhydrazone glyoxylic acid chloride; With 1-chloro-1-(dimethylamino)-2-methyl-1-propene; In dichloromethane; at 20 ℃; for 2h;

benzyl 2,6-difluoro-4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate; With N,N-dimethyl-aniline; In dichloromethane; at 0 ℃; for 0.75h;

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 1h;

Reference yield:

: (E)-2-(2-benzenesulfonylhydrazide)acetic acid

: 777089-85-7
benzyl 2,6-difluoro-4-[(1E)-3-hydroxyprop-1-enyl]phenylacrylate

: 777089-86-8
(2E)-3-{2,6-difluoro-4-[(benzyloxycarbonyl)amino]phenyl}prop-2-enyl diazoacetate

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 2,6-difluoro-4-[(1E)-3-hydroxyprop-1-enyl]phenylacrylate; With N,N-dimethyl-aniline; triethylamine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/ol050730h

Reference yield:

: 777089-82-4
4-amino-2,6-difluorobenzaldehyde

: 777089-86-8
(2E)-3-{2,6-difluoro-4-[(benzyloxycarbonyl)amino]phenyl}prop-2-enyl diazoacetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 96 percent / ethanol / 0.42 h / 23 °C

2.1: 96 percent / pyridine / CH₂Cl₂ / 17 h / 23 °C

3.1: 81 percent / DIBALH / hexane; tetrahydrofuran / 1 h / -50 °C

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

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

With pyridine; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; diisobutylaluminium hydride; In tetrahydrofuran; ethanol; hexane; dichloromethane;
DOI:10.1021/ol050730h