4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3R,4S)-4-hydroxytetrahydrofuran-3-yl]benzamide

Base Information

• Chemical Name: 4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3R,4S)-4-hydroxytetrahydrofuran-3-yl]benzamide
• CAS No.: 1421582-95-7
• Molecular Formula: C₂₆H₂₆FN₃O₆
• Molecular Weight: 495.507
• Mol file: 1421582-95-7.mol

Synonyms:4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3R,4S)-4-hydroxytetrahydrofuran-3-yl]benzamide

Chemical Property of 4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3R,4S)-4-hydroxytetrahydrofuran-3-yl]benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3R,4S)-4-hydroxytetrahydrofuran-3-yl]benzamide

There total 9 articles about 4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3R,4S)-4-hydroxytetrahydrofuran-3-yl]benzamide 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:

4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluorobenzoic acid (1371591-80-8) + (3R,4S)-4-aminotetrahydrofuran-3-ol (190792-70-2,153610-11-8,214629-29-5,330975-13-8,535936-61-9) → 4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3S,4R)-4-hydroxytetrahydrofuran-3-yl]benzamide (1421582-94-6) + 4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3R,4S)-4-hydroxytetrahydrofuran-3-yl]benzamide (1421582-95-7)

Guidance literature:

4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluorobenzoic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

(3R,4S)-4-aminotetrahydrofuran-3-ol; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h; Overall yield = 49 %; Overall yield = 241 mg;

Reference yield:

tert-butyl 4-amino(hydroxyimino)methyl-2-fluorobenzoate (1263483-74-4) → 4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3S,4R)-4-hydroxytetrahydrofuran-3-yl]benzamide (1421582-94-6) + 4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3R,4S)-4-hydroxytetrahydrofuran-3-yl]benzamide (1421582-95-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / N,N-dimethyl-formamide / 0.5 h / 20 °C

1.2: 3.5 h / 100 °C

2.1: methanol; potassium carbonate / 0.5 h / 20 °C / Cooling with ice

3.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / tetrahydrofuran / 1 h / 20 °C

4.1: trifluoroacetic acid / dichloromethane / 0.67 h / 20 °C

5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.5 h / 20 °C

5.2: 0.5 h / 20 °C

With methanol; di-tert-butyl-diazodicarboxylate; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

γ-chloro-4-hydroxybutyrophenone (7150-55-2) → 4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3S,4R)-4-hydroxytetrahydrofuran-3-yl]benzamide (1421582-94-6) + 4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3R,4S)-4-hydroxytetrahydrofuran-3-yl]benzamide (1421582-95-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydroxide / water / 6 h / 20 °C / Cooling with ice

2.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / tetrahydrofuran / 1 h / 20 °C

3.1: trifluoroacetic acid / dichloromethane / 0.67 h / 20 °C

4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.5 h / 20 °C

4.2: 0.5 h / 20 °C

With di-tert-butyl-diazodicarboxylate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

tert-butyl 4-amino(hydroxyimino)methyl-2-fluorobenzoate

γ-chloro-4-hydroxybutyrophenone

cyclopropyl 4-hydroxyphenyl ketone

tert-butyl 4-{5-[(1S)-1-acetoxypropyl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoate