(S)-(+)-2-ethoxy-4-[N-[1-(2-piperidino-phenyl)-3-methyl-1-butyl]amino-carbonylmethyl]benzoic acid

Base Information

• Chemical Name: (S)-(+)-2-ethoxy-4-[N-[1-(2-piperidino-phenyl)-3-methyl-1-butyl]amino-carbonylmethyl]benzoic acid
• CAS No.: 108157-53-5
• Molecular Formula: C₂₇H₃₆N₂O₄
• Molecular Weight: 452.594
• Mol file: 108157-53-5.mol

Synonyms:(S)-(+)-2-ethoxy-4-[N-[1-(2-piperidino-phenyl)-3-methyl-1-butyl]amino-carbonylmethyl]benzoic acid

Chemical Property of (S)-(+)-2-ethoxy-4-[N-[1-(2-piperidino-phenyl)-3-methyl-1-butyl]amino-carbonylmethyl]benzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(+)-2-ethoxy-4-[N-[1-(2-piperidino-phenyl)-3-methyl-1-butyl]amino-carbonylmethyl]benzoic acid

There total 14 articles about (S)-(+)-2-ethoxy-4-[N-[1-(2-piperidino-phenyl)-3-methyl-1-butyl]amino-carbonylmethyl]benzoic acid 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: 88.0%

ethyl 2-ethoxy-4-<2-<<3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>amino>-2-oxoethyl>-benzoate (108175-51-5) → (S)-(+)-2-ethoxy-4-[N-[1-(2-piperidino-phenyl)-3-methyl-1-butyl]amino-carbonylmethyl]benzoic acid (108157-53-5)

Guidance literature:

With sodium hydroxide; In ethanol; at 60 ℃; for 4h;

DOI:10.1021/jm9810349

Reference yield:

2-(piperidin-1-yl)benzonitrile (72752-52-4) → (S)-(+)-2-ethoxy-4-[N-[1-(2-piperidino-phenyl)-3-methyl-1-butyl]amino-carbonylmethyl]benzoic acid (108157-53-5)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran; toluene / 3 h / Heating

2: NaBH₄ / methanol / 2 h / 15 °C

3: 85 percent / PPh₃, Et₃N, CCl₄ / acetonitrile / 15 h / Ambient temperature

4: 88 percent / 1N NaOH / ethanol / 4 h / 60 °C

With tetrachloromethane; sodium hydroxide; sodium tetrahydroborate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; toluene; acetonitrile;

DOI:10.1021/jm9810349

Reference yield:

2-hydroxy-p-toluic acid (50-85-1) → (S)-(+)-2-ethoxy-4-[N-[1-(2-piperidino-phenyl)-3-methyl-1-butyl]amino-carbonylmethyl]benzoic acid (108157-53-5)

Guidance literature:

Multi-step reaction with 7 steps

1: K₂CO₃ / diethyl ether / 30 h / 150 °C

2: N-bromosuccinimide, 2,2'-azo-bis-(isobutyronitril) / CCl₄

3: 97 percent / aq. N-benzyl-tri-n-butylammonium-chloride / CH₂Cl₂ / 43 h / 20 °C

4: HCl / Heating

5: 59 percent / NaOH / ethanol / 1.5 h / 23 - 25 °C

6: 85 percent / PPh₃, Et₃N, CCl₄ / acetonitrile / 15 h / Ambient temperature

7: 88 percent / 1N NaOH / ethanol / 4 h / 60 °C

With hydrogenchloride; tetrachloromethane; sodium hydroxide; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); benzyltri(n-butyl)ammonium chloride; potassium carbonate; triethylamine; triphenylphosphine; In tetrachloromethane; diethyl ether; ethanol; dichloromethane; acetonitrile;

DOI:10.1021/jm9810349

upstream raw materials:

ethyl 2-ethoxy-4-<2-<<3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>amino>-2-oxoethyl>-benzoate

piperidine

2-(piperidin-1-yl)benzonitrile

2-Chlorobenzonitrile

Downstream raw materials:

2-ethoxy-4-{[3-methyl-1-(2-piperidin-1-ylphenyl)butylcarbamoyl]methyl}benzoic acid sodium salt

phosphoric acid salt of 2-ethoxy-4-{[3-methyl-1-(2-piperidin-1-yl-phenyl)-butylcarbamoyl]-methyl}-benzoic acid

(S)-repaglinide