{1-[1-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethylsulfanylmethyl]-cyclopropyl}-acetic acid benzyl ester

Base Information

• Chemical Name: {1-[1-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethylsulfanylmethyl]-cyclopropyl}-acetic acid benzyl ester
• CAS No.: 904916-27-4
• Molecular Formula: C₄₀H₃₃ClN₂O₄S
• Molecular Weight: 673.232
• Mol file: 904916-27-4.mol

Synonyms:{1-[1-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethylsulfanylmethyl]-cyclopropyl}-acetic acid benzyl ester

Chemical Property of {1-[1-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethylsulfanylmethyl]-cyclopropyl}-acetic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {1-[1-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethylsulfanylmethyl]-cyclopropyl}-acetic acid benzyl ester

There total 9 articles about {1-[1-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethylsulfanylmethyl]-cyclopropyl}-acetic acid benzyl 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: 46.0%

benzyl (1-mercaptomethylcyclopropyl)acetate + (+/-)-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}-2-phthalimidoethyl methanesulfonate (203940-23-2) → {1-[1-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethylsulfanylmethyl]-cyclopropyl}-acetic acid benzyl ester (904916-27-4)

Guidance literature:

With caesium carbonate; In dimethyl sulfoxide; at 20 ℃; for 1h;

DOI:10.1248/cpb.54.603

Reference yield:

methyl 3-[(E)-2-(7-chloro-2-quinolyl)vinyl]benzoate (203940-17-4) → {1-[1-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethylsulfanylmethyl]-cyclopropyl}-acetic acid benzyl ester (904916-27-4)

Guidance literature:

Multi-step reaction with 7 steps

1: aq. NaOH / tetrahydrofuran; methanol / 3 h / 40 °C

2: 93 percent / K₂CO₃*1.5H₂O; diphenylphosphoryl azide / dimethylformamide / 20 h / 20 °C

3: 98 percent / aq. HCl / ethanol / 6 h / Heating

4: 55 percent / sodium borohydride; potassium carbonate / ethanol / 1 h / 20 °C

5: 18.8 g / toluene / 3 h / 160 °C / 3 Torr

6: 19.0 g / pyridine / 1,2-dichloro-ethane / 12 h / 20 °C

7: 46 percent / cesium carbonate / dimethylsulfoxide / 1 h / 20 °C

With pyridine; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; diphenylphosphoranyl azide; potassium carbonate; caesium carbonate; In tetrahydrofuran; methanol; ethanol; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

DOI:10.1248/cpb.54.603

Reference yield:

(+/-)-2-amino-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}ethanol (203940-21-0) → {1-[1-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethylsulfanylmethyl]-cyclopropyl}-acetic acid benzyl ester (904916-27-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 18.8 g / toluene / 3 h / 160 °C / 3 Torr

2: 19.0 g / pyridine / 1,2-dichloro-ethane / 12 h / 20 °C

3: 46 percent / cesium carbonate / dimethylsulfoxide / 1 h / 20 °C

With pyridine; caesium carbonate; In dimethyl sulfoxide; 1,2-dichloro-ethane; toluene;

DOI:10.1248/cpb.54.603

upstream raw materials:

(+/-)-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}-2-phthalimidoethyl methanesulfonate

methyl 3-[(E)-2-(7-chloro-2-quinolyl)vinyl]benzoate

(+/-)-2-amino-1-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}ethanol

ethyl 5-{3-[(E)-2-(7-chloro-2-quinolyl)vinyl]phenyl}oxazol-4-carboxylate

Downstream raw materials:

[1-(2-(4-Chloro-benzenesulfonylamino)-1-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-ethylsulfanylmethyl)-cyclopropyl]-acetic acid benzyl ester