(R)-6-(2-CHLORO-4-FLUORO-PHENYLSULFAMOYL)-CYCLOHEX-1-ENECARBOXYLIC ACID

Base Information

• Chemical Name: (R)-6-(2-CHLORO-4-FLUORO-PHENYLSULFAMOYL)-CYCLOHEX-1-ENECARBOXYLIC ACID
• CAS No.: 890155-18-7
• Molecular Formula: C13H13ClFNO4S
• Molecular Weight: 333.768
• Mol file: 890155-18-7.mol

Synonyms:(R)-6-(2-CHLORO-4-FLUORO-PHENYLSULFAMOYL)-CYCLOHEX-1-ENECARBOXYLIC ACID

Chemical Property of (R)-6-(2-CHLORO-4-FLUORO-PHENYLSULFAMOYL)-CYCLOHEX-1-ENECARBOXYLIC ACID

Chemical Property:

• Melting Point: 157.5 - 158 °C (hexane)
• PSA: 91.85000
• LogP: 3.93810

Purity/Quality:

(R)-6-(2-CHLORO-4-FLUORO-PHENYLSULFAMOYL)CYCLOHEX-1-ENECARBOXYLIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-6-(2-CHLORO-4-FLUORO-PHENYLSULFAMOYL)-CYCLOHEX-1-ENECARBOXYLIC ACID

There total 4 articles about (R)-6-(2-CHLORO-4-FLUORO-PHENYLSULFAMOYL)-CYCLOHEX-1-ENECARBOXYLIC ACID 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: 84.0%

(1'R)-1'-(4-nitrophenyl)ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate (890155-20-1) → (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylic acid (890155-18-7)

Guidance literature:

With hydrogen; acetic acid; palladium on activated charcoal; for 2h; atmospheric pressure;

DOI:10.1248/cpb.54.58

Reference yield: 48.0%

acetoxymethyl (6RS)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate (340722-42-1) → (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylic acid (890155-18-7) + (6S)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylic acid + acetoxymethyl (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate (890155-23-4)

Guidance literature:

With lipase PS-D; In water; acetone; at 28 ℃; for 17.5h;

DOI:10.1248/cpb.54.58

Reference yield:

(6RS)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylic acid (340722-43-2) → (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylic acid (890155-18-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / Cs₂CO₃; tetrabutylammonium iodide / acetonitrile / 2.5 h / 52 - 55 °C

2: Lipase PS-D / acetone; H₂O / 17.5 h / 28 °C

With lipase PS-D; tetra-(n-butyl)ammonium iodide; caesium carbonate; In water; acetone; acetonitrile;

DOI:10.1248/cpb.54.58

upstream raw materials:

acetoxymethyl (6RS)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate

(1'R)-1'-(4-nitrophenyl)ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate

(6RS)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylic acid

ethyl (6RS)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate

Downstream raw materials:

ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl) sulfamoyl] cyclohex-1-ene-1-carboxylate