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

Base Information

• Chemical Name: 4-Amino-N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide
• CAS No.: 169280-56-2
• Molecular Formula: C20H29N3O3S
• Molecular Weight: 391.535
• European Community (EC) Number: 458-140-7
• UNII: 65P19KZ7JJ
• DSSTox Substance ID: DTXSID40432427
• Wikidata: Q72437770
• Mol file: 169280-56-2.mol

Synonyms:169280-56-2;4-AMINO-N-((2R,3S)-3-AMINO-2-HYDROXY-4-PHENYLBUTYL)-N-ISOBUTYLBENZENESULFONAMIDE;4-Amino-N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)benzenesulfonamide;4-AMINO-N-[(2R,3S)-3-AMINO-2-HYDROXY-4-PHENYLBUTYL]-N-ISOBUTYLBENZENE-1-SULFONAMIDE;65P19KZ7JJ;EC 458-140-7;R-374699;4-Amino-N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-(2-methylpropyl)benzenesulfonamide;Benzenesulfonamide, 4-amino-N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-(2-methylpropyl)-;N-((2R,3S)-3-Amino-2-hydroxy-4-phenylbutyl)-N-(2- methylpropyl)-4-aminobenzenesulfonamide;4-amino-n-((2r,3s)-3-amino-2-hydroxy-4-phenylbutyl)-n-isobutylbenzene-1-sulfonamide;benzenesulfonamide, 4-amino-N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(2-methylpropyl)-;UNII-65P19KZ7JJ;SCHEMBL1051190;DARUNAVIR METABOLITE M19;DTXSID40432427;AMY39010;BCP08466;MFCD16251177;AKOS015901571;DS-14175;CS-0021269;O11158;A854413;R374699;J-514438;(2R,3S)-N-(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-amino-benzenesulfonamide;4-amino-N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-(isobutyl)benzene sulfonamide;4-amino-N-((2r,3s)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzene sulfonamide;4-Amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-benzene sulfonamide;4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-benzenesulfonamide;4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide;4-Amino-n-[(2r,3s)-3-amino-2-hydroxy-4-phenylbutyl]-n-isobutylbenzene-1-sulfonamidea

Chemical Property of 4-Amino-N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide

Chemical Property:

• Refractive Index: 1.605
• Boiling Point: 609.105 °C at 760 mmHg
• PKA: 11.99±0.45(Predicted)
• Flash Point: 322.175 °C
• PSA: 118.03000
• Density: 1.226 g/cm³
• LogP: 4.20870
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly) DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 391.19296297
• Heavy Atom Count: 27
• Complexity: 521

Purity/Quality:

97%~102% ^*data from raw suppliers

4-Amino-N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CN(CC(C(CC1=CC=CC=C1)N)O)S(=O)(=O)C2=CC=C(C=C2)N
• Isomeric SMILES: CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)N)O)S(=O)(=O)C2=CC=C(C=C2)N
• Uses: A metabolite of Darunavir. Amprenavir, Darunavir and Fosamprenavir intermediate

Technology Process of 4-Amino-N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide

There total 44 articles about 4-Amino-N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide 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: 99.4%

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester (191226-98-9) → 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide (169280-56-2)

Guidance literature:

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester; With palladium 10% on activated carbon; ammonium formate; acetic acid; In tetrahydrofuran; at 15 - 20 ℃; Large scale;

With hydrogenchloride; In tetrahydrofuran; water; at 35 - 45 ℃; Large scale;

Reference yield: 96.0%

3-S-(N-tert-butyloxyformamido)-[2R-hydroxy-1-[(4-aminophenylsulfonyl)(2-methylpropyl)]amino]-4-phenylbutane (183004-94-6) → 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide (169280-56-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 4h;

DOI:10.1016/j.bmcl.2005.03.008

Reference yield: 95.0%

N-(3-dibenzylamino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitrobenzenesulfonamide (244641-42-7) → 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide (169280-56-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃;

DOI:10.1021/jm049560p

upstream raw materials:

N-(3-dibenzylamino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitrobenzenesulfonamide

4-nitro-N-((2R(syn),3S)-3-(N-benzyloxycarbonylamino)-2-hydroxy-4-phenylbutyl)-N-isobutyl-benzenesulfonamide

3-S-(N-tert-butyloxyformamido)-[2R-hydroxy-1-[(4-aminophenylsulfonyl)(2-methylpropyl)]amino]-4-phenylbutane

[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester

Downstream raw materials:

Benzothiazole-6-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-isobutyl-amide

3-S-amino-2R-hydroxy-1-[(2-aminobenzothiazol-6-sulfonyl)(2-methylpropyl)amino]-4-phenylbutane

N-[(1S,2R)-3-[(6-benzothiazolylsulfonyl)-(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-carbamic acid-1,1-dimethylethyl ester

3-S-(N-t-butyloxyformamido)-2R-hydroxy-1-[(2-aminobenzothiazol-6-sulfonyl)(2-methylpropyl)amino]-4-phenylbutane

Refernces

• 1、 Zhu, Mei,Shan, Qi,Ma, Ling,Wen, Jiajia,Dong, Biao,Zhang, Guoning,Wang, Minghua,Wang, Juxian,Zhou, Jinming,Cen, Shan,Wang, Yucheng. "Design and biological evaluation of cinnamic and phenylpropionic amide derivatives as novel dual inhibitors of HIV-1 protease and reverse transcriptase". . . Retrieved 2021/05/04.
• 2、 -. "Nitrogen-containing heterocyclic amino derivative, preparation method thereof and anti-HIV-1 medicine". Paragraph 0393-0395; 0404-0406. . Retrieved 2021/08/21.