(4R,5S)-1-((R)-2-Ethyl-pent-4-enoyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one

Base Information

• Chemical Name: (4R,5S)-1-((R)-2-Ethyl-pent-4-enoyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one
• CAS No.: 194653-94-6
• Molecular Formula: C₁₈H₂₄N₂O₂
• Molecular Weight: 300.401
• Mol file: 194653-94-6.mol

Synonyms:(4R,5S)-1-((R)-2-Ethyl-pent-4-enoyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one

Chemical Property of (4R,5S)-1-((R)-2-Ethyl-pent-4-enoyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-1-((R)-2-Ethyl-pent-4-enoyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one

There total 1 articles about (4R,5S)-1-((R)-2-Ethyl-pent-4-enoyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 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: 94.0%

allyl bromide (106-95-6) + (4R,5S)-1-Butyryl-3,4-dimethyl-5-phenyl-imidazolidin-2-one → (4R,5S)-1-((R)-2-Ethyl-pent-4-enoyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one (194653-94-6)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

DOI:10.1002/anie.199714861

Reference yield: 61.0%

(4R,5S)-1-((R)-2-Ethyl-pent-4-enoyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one (194653-94-6) + benzyl alcohol (100-51-6,185532-71-2) → (R)-2-Ethyl-pent-4-enoic acid benzyl ester (194653-95-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at 0 ℃;

DOI:10.1002/anie.199714861

Reference yield:

(4R,5S)-1-((R)-2-Ethyl-pent-4-enoyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one (194653-94-6) → (3R,6R,7R,10R,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-3,11-diethyl-7-methyl-2-oxo-azacyclotetradecane-6-carboselenoic acid Se-phenyl ester (194654-06-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 61 percent / N-BuLi / tetrahydrofuran / 0 °C

2: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C

3: 87 percent / NaTeH, piperidine, HOAc / ethanol

4: 75 percent / <(dba)3Pd₂*CHCl₃>, 4-ethyl-2,6,7-trioxa-1-phosphabicyclo<2.2.2>octane / tetrahydrofuran / 12 h / Ambient temperature

5: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

6: aq. HCO₂NH₄ / 1.5percent Pd/C / 3000240 Torr / Ambient temperature

7: PyBroP, (i-Pr)2NEt, DMAP / toluene / 83 °C

8: 1.) aq. LiOH / 1.) r.t., 4 kbar, 2.) DMSO, 120 deg C

9: TBAF / tetrahydrofuran / 0 - 40 °C

10: H₂ / 10percent Pd/C / ethanol / Ambient temperature

11: 2,6-lutidine / CH₂Cl₂ / 0 °C

12: aq. LiOH, KCN / methanol; tetrahydrofuran / Ambient temperature

13: 1.) PhOP(O)Cl₂, Et₃N, 2.) Et₃N / 1.) THF, 0 deg C, 2.) 0 deg C

With piperidine; 2,6-dimethylpyridine; dmap; potassium cyanide; lithium hydroxide; n-butyllithium; sodium hydrogen telluride; tetrabutyl ammonium fluoride; hydrogen; ammonium formate; ozone; acetic acid; O-phenyl phosphorodichloridate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium on activated charcoal; ethriol phosphite; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene;

DOI:10.1002/anie.199714861

upstream raw materials:

allyl bromide

Downstream raw materials:

(R)-2-Ethyl-pent-4-enoic acid benzyl ester

(R)-2-Ethyl-4-oxo-butyric acid benzyl ester

(R)-4-(2,2-Dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-2-ethyl-butyric acid benzyl ester

(3R,6R,7R,10R,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-3,11-diethyl-7-methyl-2-oxo-azacyclotetradecane-6-carboselenoic acid Se-phenyl ester