{[4-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazole-3-carbonyl]-amino}-acetic acid

Base Information

• Chemical Name: {[4-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazole-3-carbonyl]-amino}-acetic acid
• CAS No.: 869588-34-1
• Molecular Formula: C₂₇H₃₅F₂N₃O₄Si
• Molecular Weight: 531.675

Synonyms:{[4-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazole-3-carbonyl]-amino}-acetic acid

Chemical Property of {[4-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazole-3-carbonyl]-amino}-acetic acid

Chemical Property:

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Technology Process of {[4-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazole-3-carbonyl]-amino}-acetic acid

There total 9 articles about {[4-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazole-3-carbonyl]-amino}-acetic 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: 75.0%

[(3S,4R)-4-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone (869588-33-0) + glycine (56-40-6,18875-39-3,25718-94-9) → {[4-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazole-3-carbonyl]-amino}-acetic acid (869588-34-1)

Guidance literature:

With potassium cyanide; In methanol; at 50 ℃; for 19h;

DOI:10.1039/b510100j

Reference yield:

4-benzyloxy-1-(4-fluorophenyl)but-2-yn-1-ol (869588-29-4) → {[4-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazole-3-carbonyl]-amino}-acetic acid (869588-34-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: imidazole / dimethylformamide / 3.5 h

2.1: Na₂CO₃; H₂ / Pd/C / ethanol / 19 h

3.1: 3.643 g / H₂ / Pd/C / ethanol / 2.25 h

4.1: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

5.1: 71 percent / DBU; LiCl / acetonitrile / 2.5 h / 20 °C

6.1: toluene; hexane / 64 h / 20 °C

6.2: 84 percent / TFA / CH₂Cl₂ / 0.33 h

7.1: Mg; I₂ / diethyl ether / 1.33 h

7.2: BiCl₃ / diethyl ether / 4 h / Heating

7.3: 320.8 mg / Cu(OAc)2; Et₃N / CH₂Cl₂ / 12.5 h / 20 °C

8.1: 75 percent / KCN / methanol / 19 h / 50 °C

With 1H-imidazole; potassium cyanide; hydrogen; iodine; sodium carbonate; Dess-Martin periodane; magnesium; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; palladium on activated charcoal; In methanol; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 4.1: Dess-Martin oxidation / 5.1: Horner-Wadsworth-Emmons olefination;

DOI:10.1039/b510100j

Reference yield:

[4-benzyloxy-1-(4-fluoro-phenyl)-but-2-ynyloxy]-tert-butyl-dimethyl-silane → {[4-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazole-3-carbonyl]-amino}-acetic acid (869588-34-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Na₂CO₃; H₂ / Pd/C / ethanol / 19 h

2.1: 3.643 g / H₂ / Pd/C / ethanol / 2.25 h

3.1: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

4.1: 71 percent / DBU; LiCl / acetonitrile / 2.5 h / 20 °C

5.1: toluene; hexane / 64 h / 20 °C

5.2: 84 percent / TFA / CH₂Cl₂ / 0.33 h

6.1: Mg; I₂ / diethyl ether / 1.33 h

6.2: BiCl₃ / diethyl ether / 4 h / Heating

6.3: 320.8 mg / Cu(OAc)2; Et₃N / CH₂Cl₂ / 12.5 h / 20 °C

7.1: 75 percent / KCN / methanol / 19 h / 50 °C

With potassium cyanide; hydrogen; iodine; sodium carbonate; Dess-Martin periodane; magnesium; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; palladium on activated charcoal; In methanol; diethyl ether; ethanol; hexane; dichloromethane; toluene; acetonitrile; 3.1: Dess-Martin oxidation / 4.1: Horner-Wadsworth-Emmons olefination;

DOI:10.1039/b510100j

upstream raw materials:

[(3S,4R)-4-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone

glycine

4-(tert-butyl-dimethyl-silanyloxy)-4-(4-fluoro-phenyl)-butyraldehyde

4-benzyloxy-1-(4-fluorophenyl)but-2-yn-1-ol

Downstream raw materials:

benzenesulfonic acid 2-[4-[3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-phenyl)-propyl]-2-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-oxazol-5-yl ester

2-{2-(4-fluorophenyl)-4-[3-(4-fluorophenyl)-3-hydroxypropyl]-3,4-dihydro-2H-pyrazol-3-yl}-4H-oxazol-5-one

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