(2R)-N-hydroxy-3-methyl-2-[(4-phenylphenyl)sulfonyl-propan-2-yloxyamino]butanamide

Base Information

• Chemical Name: (2R)-N-hydroxy-3-methyl-2-[(4-phenylphenyl)sulfonyl-propan-2-yloxyamino]butanamide
• CAS No.: 849773-64-4
• Molecular Formula: C₂₀H₂₆N₂O₅S
• Molecular Weight: 406.503
• European Community (EC) Number: 635-896-8
• ChEMBL ID: CHEMBL179288
• DSSTox Substance ID: DTXSID60461471
• Pharos Ligand ID: ZGNTZ7MMS5B9
• Wikidata: Q27165008
• Mol file: 849773-64-4.mol

Synonyms:ARP 101;849773-63-3;849773-64-4;ARP-101;(R)-N-HYDROXY-2-(N-ISOPROPOXYBIPHENYL-4-YLSULFONAMIDO)-3-METHYLBUTANAMIDE;(2R)-N-hydroxy-3-methyl-2-[(4-phenylphenyl)sulfonyl-propan-2-yloxyamino]butanamide;ARP101;CHEMBL179288;(2R)-2-[([1,1'-Biphenyl]-4-ylsulfonyl)(1-methylethoxy)amino]-N-hydroxy-3-methyl-butanamide;SCHEMBL13738485;CHEBI:93296;DTXSID60461471;HMS3269F17;ZIB77363;BDBM50161330;MFCD09753277;AKOS024457201;LP00963;SDCCGSBI-0633772.P001;NCGC00186031-01;ARP 101, >=98% (HPLC), solid;HY-101535;CS-0021677;BRD-K73395020-001-01-5;Q27165008;N(2)-([biphenyl]-4-ylsulfonyl)-N-hydroxy-N(2)-isopropoxy-D-valinamide;(R)-2-[(Biphenyl-4-sulfonyl)-isopropoxy-amino]-N-hydroxy-3-methyl-butyramide;(R)-N-Hydroxy-2-(N-isopropoxy-[1,1'-biphenyl]-4-sulfonamido)-3-methylbutanamide;N(2)-([biphenyl]-4-ylsulfonyl)-N-hydroxy-N(2)-(propan-2-yloxy)-D-valinamide;N73

Chemical Property of (2R)-N-hydroxy-3-methyl-2-[(4-phenylphenyl)sulfonyl-propan-2-yloxyamino]butanamide

Chemical Property:

• PSA: 104.32000
• LogP: 4.68600
• Storage Temp.: −20°C
• Solubility.: DMSO: >20mg/mL
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 406.15624311
• Heavy Atom Count: 28
• Complexity: 588

Purity/Quality:

97% ^*data from raw suppliers

ARP 101 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)NO)N(OC(C)C)S(=O)(=O)C1=CC=C(C=C1)C2=CC=CC=C2
• Isomeric SMILES: CC(C)[C@H](C(=O)NO)N(OC(C)C)S(=O)(=O)C1=CC=C(C=C1)C2=CC=CC=C2
• Uses: ARP 101i inhibits α-MSH-stimulated melanogenesis by regulation of autophagy in melanocytes and also induces autophagy in various cancer cells.

Technology Process of (2R)-N-hydroxy-3-methyl-2-[(4-phenylphenyl)sulfonyl-propan-2-yloxyamino]butanamide

There total 9 articles about (2R)-N-hydroxy-3-methyl-2-[(4-phenylphenyl)sulfonyl-propan-2-yloxyamino]butanamide 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: 48.0%

(R)-N-(tert-butyldimethylsilyloxy)-2-(N-isopropoxybiphenyl-4-ylsulfonamido)-3-methylbutanamide (849773-59-7) → ARP101 (849773-63-3,849773-64-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 5h;

DOI:10.1016/j.bmc.2006.01.056

Reference yield:

N-isopropoxy-1,1'-biphenyl-4-sulfonamide (704888-95-9) → ARP101 (849773-63-3,849773-64-4)

Guidance literature:

Multi-step reaction with 3 steps

1: caesium carbonate; tetrabutylammonium hydrogen sulfate / dimethylformamide / 3 h / 20 °C

2: 30 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 20 h / 20 °C

3: 48 percent / trifluoroacetic acid / CH₂Cl₂ / 5 h / 0 °C

With tetra(n-butyl)ammonium hydrogensulfate; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2006.01.056

Reference yield:

(S)-2-Hydroxy-3-methylbutanoic acid (17407-55-5) → ARP101 (849773-63-3,849773-64-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / 18 h / 20 °C

2: toluene / 3 h / 95 °C

3: LiOH / H₂O; methanol; tetrahydrofuran / 3 h / 20 °C

4: 53 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 5 h / 0 °C

5: 30 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 20 h / 20 °C

6: 48 percent / trifluoroacetic acid / CH₂Cl₂ / 5 h / 0 °C

With lithium hydroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 4: Mitsunobu reaction;

DOI:10.1016/j.bmc.2006.01.056

upstream raw materials:

(R)-N-(tert-butyldimethylsilyloxy)-2-(N-isopropoxybiphenyl-4-ylsulfonamido)-3-methylbutanamide

(S)-2-Hydroxy-3-methylbutanoic acid

L-α-hydroxyisovaleric acid t-butyl ester

(S)-tert-butyl 2-bromo-3-methylbutanoate