2-(benzhydrylidene-amino)-3-[8-(tert-butyl-diphenyl-silanyloxy)-5-dimethylsulfamoyl-quinolin-2-yl]-propionic acid tert-butyl ester

Base Information

• Chemical Name: 2-(benzhydrylidene-amino)-3-[8-(tert-butyl-diphenyl-silanyloxy)-5-dimethylsulfamoyl-quinolin-2-yl]-propionic acid tert-butyl ester
• CAS No.: 607708-60-1
• Molecular Formula: C₄₇H₅₁N₃O₅SSi
• Molecular Weight: 798.091
• Mol file: 607708-60-1.mol

Synonyms:2-(benzhydrylidene-amino)-3-[8-(tert-butyl-diphenyl-silanyloxy)-5-dimethylsulfamoyl-quinolin-2-yl]-propionic acid tert-butyl ester

Chemical Property of 2-(benzhydrylidene-amino)-3-[8-(tert-butyl-diphenyl-silanyloxy)-5-dimethylsulfamoyl-quinolin-2-yl]-propionic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(benzhydrylidene-amino)-3-[8-(tert-butyl-diphenyl-silanyloxy)-5-dimethylsulfamoyl-quinolin-2-yl]-propionic acid tert-butyl ester

There total 6 articles about 2-(benzhydrylidene-amino)-3-[8-(tert-butyl-diphenyl-silanyloxy)-5-dimethylsulfamoyl-quinolin-2-yl]-propionic acid tert-butyl 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:

N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) + 8-tert-butyldiphenylsilyloxy-5-(N,N-dimethyl)sulfonamide-2-(hydroxymethyl)quinoline (607708-59-8) → 2-(benzhydrylidene-amino)-3-[8-(tert-butyl-diphenyl-silanyloxy)-5-dimethylsulfamoyl-quinolin-2-yl]-propionic acid tert-butyl ester (607708-60-1)

Guidance literature:

With (1S,2S,4S,5R)-2-((R)-(allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide; cesium hydrochloride monohydrate; In dichloromethane; at -78 - -55 ℃; for 51h;

DOI:10.1021/ja0355980

Reference yield:

5-(N,N-dimethyl)sulfonamido-8-hydroxy-2-methylquinoline (349543-92-6) → 2-(benzhydrylidene-amino)-3-[8-(tert-butyl-diphenyl-silanyloxy)-5-dimethylsulfamoyl-quinolin-2-yl]-propionic acid tert-butyl ester (607708-60-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 57 percent / imidazole / dimethylformamide / 2 h

2: 4A moleculer sieves; selenium dioxide / dioxane / 17 h / 95 °C

3: sodium borohydride / ethanol; CH₂Cl₂ / 0.25 h

4: 538 mg / N-bromosuccinimide; triphenylphosphine / CH₂Cl₂ / 4 h / 0 °C

5: (8S,9R)-O-⁽⁹⁾-allyl-N-9-anthracenyl methylcinchonidium Br; cesium hydrochloride monohydrate / CH₂Cl₂ / 51 h / -78 - -55 °C

With 1H-imidazole; sodium tetrahydroborate; N-Bromosuccinimide; selenium(IV) oxide; (1S,2S,4S,5R)-2-((R)-(allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide; 4 A molecular sieve; cesium hydrochloride monohydrate; triphenylphosphine; In 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja0355980

Reference yield:

8-hydroxy-2-methyl-quinoline-5-sulfonyl chloride (903877-94-1) → 2-(benzhydrylidene-amino)-3-[8-(tert-butyl-diphenyl-silanyloxy)-5-dimethylsulfamoyl-quinolin-2-yl]-propionic acid tert-butyl ester (607708-60-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / tetrahydrofuran / 3.17 h

2: 57 percent / imidazole / dimethylformamide / 2 h

3: 4A moleculer sieves; selenium dioxide / dioxane / 17 h / 95 °C

4: sodium borohydride / ethanol; CH₂Cl₂ / 0.25 h

5: 538 mg / N-bromosuccinimide; triphenylphosphine / CH₂Cl₂ / 4 h / 0 °C

6: (8S,9R)-O-⁽⁹⁾-allyl-N-9-anthracenyl methylcinchonidium Br; cesium hydrochloride monohydrate / CH₂Cl₂ / 51 h / -78 - -55 °C

With 1H-imidazole; sodium tetrahydroborate; N-Bromosuccinimide; selenium(IV) oxide; (1S,2S,4S,5R)-2-((R)-(allyloxy)(quinolin-4-yl)methyl)-1-(anthracen-9-ylmethyl)-5-vinylquinuclidin-1-ium bromide; 4 A molecular sieve; cesium hydrochloride monohydrate; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja0355980

upstream raw materials:

N-(diphenylmethylene)glycine tert-butyl ester

8-tert-butyldiphenylsilyloxy-5-(N,N-dimethyl)sulfonamide-2-(hydroxymethyl)quinoline

5-(N,N-dimethyl)sulfonamido-8-hydroxy-2-methylquinoline

8-hydroxy-2-methyl-quinoline-5-sulfonyl chloride

Downstream raw materials:

(S)-2-amino-N^α-(9-fluorenylmethyloxycarbonyl)-3-(8-hydroxy-5-(N,N-dimethyl)sylfonamidoquinoline-2-yl)propionic acid