ethyl (3S)-1-[(2S)-2-hydroxy-2-(4-{5-[3-phenyl-4-(trifluoromethyl)isoxazol-5-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]piperidine-3-carboxylate

Base Information

• Chemical Name: ethyl (3S)-1-[(2S)-2-hydroxy-2-(4-{5-[3-phenyl-4-(trifluoromethyl)isoxazol-5-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]piperidine-3-carboxylate
• CAS No.: 1265323-50-9
• Molecular Formula: C₂₈H₂₇F₃N₄O₅
• Molecular Weight: 556.541
• Mol file: 1265323-50-9.mol

Synonyms:ethyl (3S)-1-[(2S)-2-hydroxy-2-(4-{5-[3-phenyl-4-(trifluoromethyl)isoxazol-5-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]piperidine-3-carboxylate

Chemical Property of ethyl (3S)-1-[(2S)-2-hydroxy-2-(4-{5-[3-phenyl-4-(trifluoromethyl)isoxazol-5-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]piperidine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (3S)-1-[(2S)-2-hydroxy-2-(4-{5-[3-phenyl-4-(trifluoromethyl)isoxazol-5-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]piperidine-3-carboxylate

There total 12 articles about ethyl (3S)-1-[(2S)-2-hydroxy-2-(4-{5-[3-phenyl-4-(trifluoromethyl)isoxazol-5-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]piperidine-3-carboxylate 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: 36.0%

3-phenyl-4-(trifluoromethyl)isoxazole-5-carbonyl fluoride (1236188-83-2) + ethyl (3S)-1-((2S)-2-hydroxy-2-(4-((Z)-N'-hydroxycarbamimidoyl)-phenyl)ethyl)piperidine-3-carboxylate (1265750-06-8) → ethyl (3S)-1-[(2S)-2-hydroxy-2-(4-{5-[3-phenyl-4-(trifluoromethyl)isoxazol-5-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]piperidine-3-carboxylate (1265323-50-9)

Guidance literature:

3-phenyl-4-(trifluoromethyl)isoxazole-5-carbonyl fluoride; ethyl (3S)-1-((2S)-2-hydroxy-2-(4-((Z)-N'-hydroxycarbamimidoyl)-phenyl)ethyl)piperidine-3-carboxylate; With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 2h; Inert atmosphere;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; acetonitrile; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.6b00373

Reference yield:

syn-benzaldehyde oxime (932-90-1,622-31-1,140461-24-1,140461-25-2,622-32-2) → ethyl (3S)-1-[(2S)-2-hydroxy-2-(4-{5-[3-phenyl-4-(trifluoromethyl)isoxazol-5-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]piperidine-3-carboxylate (1265323-50-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N-chloro-succinimide / N,N-dimethyl-formamide / 20 °C

2.1: 1,1-dichloroethane / 20 - 70 °C

3.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; disodium hydrogenphosphate; sodium chlorite; sodium dihydrogenphosphate / acetonitrile; water / 20 - 35 °C

4.1: pyridine; trifluoro-[1,3,5]triazine / 20 °C

5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 2 h

5.2: 20 °C

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; disodium hydrogenphosphate; sodium dihydrogenphosphate; N-chloro-succinimide; trifluoro-[1,3,5]triazine; N-ethyl-N,N-diisopropylamine; In 1,1-dichloroethane; water; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

4-Cyanophenacyl bromide (20099-89-2) → ethyl (3S)-1-[(2S)-2-hydroxy-2-(4-{5-[3-phenyl-4-(trifluoromethyl)isoxazol-5-yl]-1,2,4-oxadiazol-3-yl}phenyl)ethyl]piperidine-3-carboxylate (1265323-50-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: toluene

2.1: sodium tetrahydroborate / toluene; methanol / 1 h

3.1: hydroxylamine hydrochloride; sodium hydrogencarbonate / isopropyl alcohol / 85 °C

4.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 2 h

4.2: 20 °C

With sodium tetrahydroborate; hydroxylamine hydrochloride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; In methanol; isopropyl alcohol; toluene; acetonitrile;

upstream raw materials:

4-Cyanophenacyl bromide

phenylhydroxamoyl chloride

syn-benzaldehyde oxime

(S)-(+)-2-(4-cyanophenyl)oxirane