1-{(2R)-4-[5-(4-fluorophenoxy)furan-2-yl]but-3-yn-2-yl}-1-hydroxyurea

Base Information

• Chemical Name: 1-{(2R)-4-[5-(4-fluorophenoxy)furan-2-yl]but-3-yn-2-yl}-1-hydroxyurea
• CAS No.: 141579-87-5
• Molecular Formula: C₁₅H₁₃FN₂O₄
• Molecular Weight: 304.278
• Mol file: 141579-87-5.mol

Synonyms:Urea,N-[(1R)-3-[5-(4-fluorophenoxy)-2-furanyl]-1-methyl-2-propynyl]-N-hydroxy-(9CI); Urea,N-[3-[5-(4-fluorophenoxy)-2-furanyl]-1-methyl-2-propynyl]-N-hydroxy-, (R)-; A79175; Abbott 79175

Chemical Property of 1-{(2R)-4-[5-(4-fluorophenoxy)furan-2-yl]but-3-yn-2-yl}-1-hydroxyurea

Chemical Property:

• Vapor Pressure: 9.5E-10mmHg at 25°C
• Boiling Point: 472.9°Cat760mmHg
• Flash Point: 239.8°C
• Density: 1.42g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{(2R)-4-[5-(4-fluorophenoxy)furan-2-yl]but-3-yn-2-yl}-1-hydroxyurea

There total 29 articles about 1-{(2R)-4-[5-(4-fluorophenoxy)furan-2-yl]but-3-yn-2-yl}-1-hydroxyurea 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: 86.0%

(R)-(+)-N-hydroxy-N-(3-butyn-2-yl)urea (154355-92-7) + 5-(4-fluorophenoxy)-2-iodofuran (176965-99-4) → (R)-(+)-N-<3-<5-(4-fluorophenoxy)methyl>-2-furyl>-1-methyl-2-propynyl-N-hydroxyurea (141579-87-5) + (R)-5-[5-(4-Fluoro-phenoxy)-furan-2-yl]-3-methyl-3H-isoxazole-2-carboxylic acid amide

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); copper(l) iodide; diisopropylamine; triphenylphosphine; In ethyl acetate; at 20 - 25 ℃; for 1.5h;

DOI:10.1016/S0957-4166(97)00159-6

Reference yield: 57.0%

N,O-bis(phenoxycarbonyl)-N-<4-<5-(4-fluorophenoxy)-2-furyl>-3-butyn-2-yl>hydroxylamine (141598-93-8) → A-78773 (141579-67-1,141579-87-5)

Guidance literature:

With ammonia; at -78 - 20 ℃;

DOI:10.1021/jm00024a004

Reference yield:

5-nitrofurane-2-carboxaldehyde (698-63-5) → A-78773 (141579-67-1,141579-87-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) sodium hydride / 1.) THF, 2.) DMF, 0.5h

2: 1.) zinc, triphenylphosphine / 1.) CH₂Cl₂, overnight, 2.) CH₂Cl₂, RT, 2 h

3: 50 percent / n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

4: 1.) lithium diisopropylamide / 1.) THF, -5 deg C, 0.5 h, 2.) THF, from -5 deg C to RT

5: 53 percent / triphenylphosphine, diisopropyl azodicarboxylate / tetrahydrofuran / 0.5 h / Ambient temperature

6: 57 percent / ammonia / -78 - 20 °C

With n-butyllithium; di-isopropyl azodicarboxylate; ammonia; sodium hydride; triphenylphosphine; zinc; lithium diisopropyl amide; In tetrahydrofuran; hexane;

DOI:10.1021/jm00024a004

upstream raw materials:

N,O-bis(phenoxycarbonyl)-N-<4-<5-(4-fluorophenoxy)-2-furyl>-3-butyn-2-yl>hydroxylamine

5-nitrofurane-2-carboxaldehyde

5-(4'-fluorophenyl)furan-2-carbaldehyde

(5-(4-fluorophenoxy)-2-furyl)acetylene

Refernces

• 1、 Kolasa, Teodozyj,Stewart, Andrew O.,Brooks, Clint D. W.. "Asymmetric synthesis of (R)-N-3-butyn-2-yl-N-hydroxyurea, a key intermediate for 5-lipoxygenase inhibitors". . p. 729 - 736. Retrieved 2007/10/03.
• 2、 Brooks,Stewart,Basha,Bhatia,Ratajczyk,Martin,Craig,Kolasa,Bouska,Lanni,Harris,Malo,Carter,Bell. "(R)-(+)-N-[3-[5-[(4-fluorophenyl)methyl]-2-thienyl]-1-methyl-2-propynyl]- N-hydroxyurea (ABT-761), a second-generation 5-lipoxygenase inhibitor". . p. 4768 - 4775. Retrieved 2007/10/03.