Benzenesulfonamide, N-[(2R,3S)-3-[bis(phenylmethyl)amino]-2-hydroxy-4-phenylbutyl]-4-meth oxy-N-(2-methylpropyl)-

Base Information

• Chemical Name: Benzenesulfonamide, N-[(2R,3S)-3-[bis(phenylmethyl)amino]-2-hydroxy-4-phenylbutyl]-4-meth oxy-N-(2-methylpropyl)-
• CAS No.: 799241-79-5
• Molecular Formula: C35H42N2O4S
• Molecular Weight: 586.795
• Mol file: 799241-79-5.mol

Synonyms:

Chemical Property of Benzenesulfonamide, N-[(2R,3S)-3-[bis(phenylmethyl)amino]-2-hydroxy-4-phenylbutyl]-4-meth oxy-N-(2-methylpropyl)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzenesulfonamide, N-[(2R,3S)-3-[bis(phenylmethyl)amino]-2-hydroxy-4-phenylbutyl]-4-meth oxy-N-(2-methylpropyl)-

There total 6 articles about Benzenesulfonamide, N-[(2R,3S)-3-[bis(phenylmethyl)amino]-2-hydroxy-4-phenylbutyl]-4-meth oxy-N-(2-methylpropyl)- 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: 71.0%

4-methoxy-phenyl-sulphonyl chloride (98-68-0) + βS--αR-<<(2-methylpropyl)amino>methyl>-benzenepropanol (169331-42-4) → N-((2R,3S)-3-(dibenzylamino)-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-methoxybenzenesulfonamide (799241-79-5)

Guidance literature:

With sodium carbonate; In dichloromethane; water; at 0 - 20 ℃; for 3h;

DOI:10.1002/cmdc.201200271

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → N-((2R,3S)-3-(dibenzylamino)-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-methoxybenzenesulfonamide (799241-79-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium hydroxide; potassium carbonate / water / 3 h / Reflux

2.1: lithium aluminium tetrahydride / diethyl ether / 0 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 - 0 °C

3.2: 1 h

4.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / -20 °C

5.1: 1H-imidazole / dichloromethane / 0 - 20 °C

6.1: diisobutylaluminium hydride / diethyl ether; hexane / 3 h / -78 °C

6.2: 3 h / 20 °C

6.3: 20 °C / Cooling with ice

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

8.1: sodium carbonate / water; dichloromethane / 3 h / 0 - 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium carbonate; potassium carbonate; dimethyl sulfoxide; sodium hydroxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; 3.1: |Swern Oxidation;

DOI:10.1002/cmdc.201200271

Reference yield:

(2S)-N,N-dibenzylphenylalaninal (123054-12-6,123808-74-2,136370-73-5,111060-64-1) → N-((2R,3S)-3-(dibenzylamino)-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-methoxybenzenesulfonamide (799241-79-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / -20 °C

2.1: 1H-imidazole / dichloromethane / 0 - 20 °C

3.1: diisobutylaluminium hydride / diethyl ether; hexane / 3 h / -78 °C

3.2: 3 h / 20 °C

3.3: 20 °C / Cooling with ice

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

5.1: sodium carbonate / water; dichloromethane / 3 h / 0 - 20 °C

With 1H-imidazole; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium carbonate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water;

DOI:10.1002/cmdc.201200271

upstream raw materials:

4-methoxy-phenyl-sulphonyl chloride

βS--αR-<<(2-methylpropyl)amino>methyl>-benzenepropanol

benzyl bromide

(S)-2-(dibenzylamino)-3-phenylpropan-1-ol

Downstream raw materials:

C₂₅H₃₉N₂O₇PS

C₂₉H₄₇N₂O₇PS

{(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl-(4-methoxy-benzenesulfonyl)-amino]-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-4-hydroxy-N-isobutylbenzenesulfonamide

Refernces

• 1、 Surleraux, Dominique L. N. G.,Tahri, Abdellah,Verschueren, Wim G.,Pille, Geert M. E.,De Kock, Herman A.,Jonckers, Tim H. M.,Peeters, Anik,De Meyer, Sandra,Azijn, Hilde,Pauwels, Rudi,De Bethune, Marie-Pierre,King, Nancy M.,Prabu-Jeyabalan, Moses,Schiffer, Celia A.,Wigerinck, Piet B. T. P.. "Discovery and selection of TMC114, a next generation HIV-1 protease inhibitor". . p. 1813 - 1822. Retrieved 2007/10/03.