(1S,2R)-N-(2-hydroxyacenaphthen-1-yl)-4-methylbenzenesulfonamide

Base Information

• Chemical Name: (1S,2R)-N-(2-hydroxyacenaphthen-1-yl)-4-methylbenzenesulfonamide
• CAS No.: 518308-44-6
• Molecular Formula: C₁₉H₁₇NO₃S
• Molecular Weight: 339.415
• Mol file: 518308-44-6.mol

Synonyms:(1S,2R)-N-(2-hydroxyacenaphthen-1-yl)-4-methylbenzenesulfonamide

Chemical Property of (1S,2R)-N-(2-hydroxyacenaphthen-1-yl)-4-methylbenzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R)-N-(2-hydroxyacenaphthen-1-yl)-4-methylbenzenesulfonamide

There total 4 articles about (1S,2R)-N-(2-hydroxyacenaphthen-1-yl)-4-methylbenzenesulfonamide 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: 77.0%

p-toluenesulfonyl chloride (98-59-9) + (1S,2R)-2-amino-1-acenaphthenol (161595-81-9) → (1S,2R)-N-(2-hydroxyacenaphthen-1-yl)-4-methylbenzenesulfonamide (518308-44-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; acetonitrile; at 0 ℃; for 4h;

DOI:10.1021/ol034086n

Reference yield:

(1S,2R)-acenaphtheno-1,3-oxazolidin-2-one (518308-42-4) → (1S,2R)-N-(2-hydroxyacenaphthen-1-yl)-4-methylbenzenesulfonamide (518308-44-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / NaOH / methanol; H₂O / 18 h / 80 °C

2: 77 percent / DMAP; Et₃N / CH₂Cl₂; acetonitrile / 4 h / 0 °C

With dmap; sodium hydroxide; triethylamine; In methanol; dichloromethane; water; acetonitrile;

DOI:10.1021/ol034086n

Reference yield:

(1R,2R)-N-tert-butyloxycarbonyl-2-amino-1-acenaphthenol (518308-41-3) → (1S,2R)-N-(2-hydroxyacenaphthen-1-yl)-4-methylbenzenesulfonamide (518308-44-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / MsCl; Et₃N / CH₂Cl₂ / 4 h / 23 °C

2: 87 percent / NaOH / methanol; H₂O / 18 h / 80 °C

3: 77 percent / DMAP; Et₃N / CH₂Cl₂; acetonitrile / 4 h / 0 °C

With dmap; sodium hydroxide; methanesulfonyl chloride; triethylamine; In methanol; dichloromethane; water; acetonitrile;

DOI:10.1021/ol034086n

upstream raw materials:

p-toluenesulfonyl chloride

(1S,2R)-2-amino-1-acenaphthenol

(1S,2R)-acenaphtheno-1,3-oxazolidin-2-one

(1R,2R)-N-tert-butyloxycarbonyl-2-amino-1-acenaphthenol

Downstream raw materials:

Propionic acid (1S,2R)-2-(toluene-4-sulfonylamino)-acenaphthen-1-yl ester

(2R,3R)-4-Benzyloxy-3-hydroxy-2-methyl-butyric acid (1S,2R)-2-(toluene-4-sulfonylamino)-acenaphthen-1-yl ester

(2R,3R)-3-Cyclohexyl-3-hydroxy-2-methyl-propionic acid (1S,2R)-2-(toluene-4-sulfonylamino)-acenaphthen-1-yl ester

(2R,3R)-3-Hydroxy-2-methyl-5-phenyl-pentanoic acid (1S,2R)-2-(toluene-4-sulfonylamino)-acenaphthen-1-yl ester