(S)-4-[[[4-(4-Fluorophenyl)-6-methyl-2-(1-methylethyl)-3-pyridinyl]ethynyl]hydroxyphosphinyl]-3-hydroxybutanoic acid, disodium salt

Base Information

• Chemical Name: (S)-4-[[[4-(4-Fluorophenyl)-6-methyl-2-(1-methylethyl)-3-pyridinyl]ethynyl]hydroxyphosphinyl]-3-hydroxybutanoic acid, disodium salt
• CAS No.: 135426-63-0
• Molecular Formula: C₂₁H₂₁FNO₅P*2Na
• Molecular Weight: 463.353
• Mol file: 135426-63-0.mol

Synonyms:

Chemical Property of (S)-4-[[[4-(4-Fluorophenyl)-6-methyl-2-(1-methylethyl)-3-pyridinyl]ethynyl]hydroxyphosphinyl]-3-hydroxybutanoic acid, disodium salt

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-[[[4-(4-Fluorophenyl)-6-methyl-2-(1-methylethyl)-3-pyridinyl]ethynyl]hydroxyphosphinyl]-3-hydroxybutanoic acid, disodium salt

There total 10 articles about (S)-4-[[[4-(4-Fluorophenyl)-6-methyl-2-(1-methylethyl)-3-pyridinyl]ethynyl]hydroxyphosphinyl]-3-hydroxybutanoic acid, disodium salt 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:

(S)-4-{[4-(4-Fluoro-phenyl)-2-isopropyl-6-methyl-pyridin-3-ylethynyl]-methoxy-phosphinoyl}-3-hydroxy-butyric acid methyl ester → (S)-4-[[[4-(4-Fluorophenyl)-6-methyl-2-(1-methylethyl)-3-pyridinyl]ethynyl]hydroxyphosphinyl]-3-hydroxybutanoic acid, disodium salt (135426-63-0)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 18h; Yield given; Ambient temperature;

DOI:10.1021/jm00113a019

Reference yield:

(E)-4-(4-fluorophenyl)but-3-en-2-one (65300-29-0) → (S)-4-[[[4-(4-Fluorophenyl)-6-methyl-2-(1-methylethyl)-3-pyridinyl]ethynyl]hydroxyphosphinyl]-3-hydroxybutanoic acid, disodium salt (135426-63-0)

Guidance literature:

Multi-step reaction with 8 steps

1: EtONa / ethanol / 4.5 h / Ambient temperature

2: NH₄OAc, Cu(OAc)2 / acetic acid / 24 h / Heating

3: 22 percent / LiAlH₄ / tetrahydrofuran / 6 h / Ambient temperature

4: oxalyl chloride, DMSO / CH₂Cl₂; tetrahydrofuran / 0.25 h / -78 °C

5: triphenylphosphine / CH₂Cl₂ / 0.42 h / Ambient temperature

6: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 50 min, 2.) THF, hexane, -78 deg C, 30 min

7: HOAc, tetra-n-butylammonium fluoride / tetrahydrofuran / 18 h / Ambient temperature

8: 1N aq. NaOH / dioxane / 18 h / Ambient temperature

With sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; copper diacetate; oxalyl dichloride; ammonium acetate; tetrabutyl ammonium fluoride; sodium ethanolate; acetic acid; dimethyl sulfoxide; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; acetic acid;

DOI:10.1021/jm00113a019

Reference yield:

4-(4-Fluorophenyl)-6-methyl-2-(1-methylethyl)-3-pyridinemethanol (122252-99-7) → (S)-4-[[[4-(4-Fluorophenyl)-6-methyl-2-(1-methylethyl)-3-pyridinyl]ethynyl]hydroxyphosphinyl]-3-hydroxybutanoic acid, disodium salt (135426-63-0)

Guidance literature:

Multi-step reaction with 5 steps

1: oxalyl chloride, DMSO / CH₂Cl₂; tetrahydrofuran / 0.25 h / -78 °C

2: triphenylphosphine / CH₂Cl₂ / 0.42 h / Ambient temperature

3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 50 min, 2.) THF, hexane, -78 deg C, 30 min

4: HOAc, tetra-n-butylammonium fluoride / tetrahydrofuran / 18 h / Ambient temperature

5: 1N aq. NaOH / dioxane / 18 h / Ambient temperature

With sodium hydroxide; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; acetic acid; dimethyl sulfoxide; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1021/jm00113a019

upstream raw materials:

(E)-4-(4-fluorophenyl)but-3-en-2-one

4-(4-Fluorophenyl)-6-methyl-2-(1-methylethyl)-3-pyridinemethanol

4-(4-Fluorophenyl)-6-methyl-2-(1-methylethyl)-3-pyridinecarboxylic acid,ethyl ester

β-(4-Fluorophenyl)-α-(2-methyl-1-oxopropyl)-Δ-oxohexanoic acid, ethyl ester