(S)-(-)-4-(1-acetoxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide

Base Information

• Chemical Name: (S)-(-)-4-(1-acetoxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide
• CAS No.: 220948-23-2
• Molecular Formula: C₁₇H₂₄N₂O₅S
• Molecular Weight: 368.454
• Mol file: 220948-23-2.mol

Synonyms:(S)-(-)-4-(1-acetoxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide

Chemical Property of (S)-(-)-4-(1-acetoxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(-)-4-(1-acetoxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide

There total 8 articles about (S)-(-)-4-(1-acetoxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide 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: 39.0%

(+/-)-4-(1-acetoxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide (220948-18-5) → (R)-(+)-4-(1-hydroxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide + (S)-(-)-4-(1-acetoxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide (220948-23-2)

Guidance literature:

With lipase Amano P; water; In di-isopropyl ether; benzene; at 40 ℃; for 240h;

DOI:10.1248/cpb.47.1164

Reference yield: 39.0%

(+/-)-4-(1-acetoxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide (220948-18-5) → (R)-(+)-4-(1-hydroxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide + (S)-(-)-4-(1-acetoxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide (220948-23-2) + (R)-(+)-4-(1-acetoxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide (220948-24-3)

Guidance literature:

With lipase Amano P; water; In di-isopropyl ether; benzene; at 40 ℃; for 240h; Title compound not separated from byproducts;

DOI:10.1248/cpb.47.1164

Reference yield:

p-ethylbenzenesulfonyl chloride (16712-69-9) → (S)-(-)-4-(1-acetoxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide (220948-23-2)

Guidance literature:

Multi-step reaction with 6 steps

1: aq. NH₃ / 0.5 h / 40 °C

2: CrO₃, aq. AcOH / 3 h / Ambient temperature

3: 95 percent / NaBH₄ / methanol / 0.5 h / 0 °C

5: 89 percent / pyridine / 2 h / -10 °C

6: 1.) 1,8-diazabicyclo<5.4.0>undec-7-ene / 1.) benzene, RT, 30 min, 2.) benzene, RT, 1 h

With pyridine; chromium(VI) oxide; ammonium hydroxide; sodium tetrahydroborate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol;

DOI:10.1016/S0957-4166(98)00436-4

upstream raw materials:

Cyclohexyl isocyanate

Acetic acid (S)-1-(4-sulfamoyl-phenyl)-ethyl ester

(+/-)-4-(1-acetoxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide

p-ethylbenzenesulfonyl chloride