4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3S,4R)-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-[(3S,4R)-4-hydroxytetrahydrofuran-3-yl]benzamide
CAS No.:1421582-94-6
Molecular Formula:C₂₆H₂₆FN₃O₆
Molecular Weight:495.507
Hs Code.:

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

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

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

: 1371591-80-8
4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluorobenzoic acid

: 190792-70-2,153610-11-8,214629-29-5,330975-13-8,535936-61-9
(3R,4S)-4-aminotetrahydrofuran-3-ol

: 1421582-94-6
4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3S,4R)-4-hydroxytetrahydrofuran-3-yl]benzamide

: 1421582-95-7
4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3R,4S)-4-hydroxytetrahydrofuran-3-yl]benzamide

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:

: 1263483-74-4
tert-butyl 4-amino(hydroxyimino)methyl-2-fluorobenzoate

: 1421582-94-6
4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3S,4R)-4-hydroxytetrahydrofuran-3-yl]benzamide

: 1421582-95-7
4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3R,4S)-4-hydroxytetrahydrofuran-3-yl]benzamide

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:

: 7150-55-2
γ-chloro-4-hydroxybutyrophenone

: 1421582-94-6
4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3S,4R)-4-hydroxytetrahydrofuran-3-yl]benzamide

: 1421582-95-7
4-(5-{(1R)-1-[4-(cyclopropylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluoro-N-[(3R,4S)-4-hydroxytetrahydrofuran-3-yl]benzamide

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;