(E)-3-[5-((E)-2-tert-Butoxycarbonylamino-vinyl)-9,9-dimethyl-9H-xanthen-4-yl]-acrylic acid ethyl ester

Base Information

• Chemical Name: (E)-3-[5-((E)-2-tert-Butoxycarbonylamino-vinyl)-9,9-dimethyl-9H-xanthen-4-yl]-acrylic acid ethyl ester
• CAS No.: 1026000-53-2
• Molecular Formula: C₂₇H₃₁NO₅
• Molecular Weight: 449.547
• Mol file: 1026000-53-2.mol

Synonyms:(E)-3-[5-((E)-2-tert-Butoxycarbonylamino-vinyl)-9,9-dimethyl-9H-xanthen-4-yl]-acrylic acid ethyl ester

Chemical Property of (E)-3-[5-((E)-2-tert-Butoxycarbonylamino-vinyl)-9,9-dimethyl-9H-xanthen-4-yl]-acrylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-[5-((E)-2-tert-Butoxycarbonylamino-vinyl)-9,9-dimethyl-9H-xanthen-4-yl]-acrylic acid ethyl ester

There total 1 articles about (E)-3-[5-((E)-2-tert-Butoxycarbonylamino-vinyl)-9,9-dimethyl-9H-xanthen-4-yl]-acrylic acid ethyl ester 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:

9,9-dimethylxanthene (19814-75-6) → (E)-3-[5-((E)-2-tert-Butoxycarbonylamino-vinyl)-9,9-dimethyl-9H-xanthen-4-yl]-acrylic acid ethyl ester (1026000-53-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-BuLi, N,N,N',N'-tetramethylethylenediamine, 2.) CH₂I₂ / 1) Et₂O, rt, 24 h; 2) Et₂O, rt, 12 h

2: 24 percent / palladium acetate, Ph₃P, Et₃N / acetonitrile / 6 h / 75 °C

3: 63 percent / palladium acetate, Ph₃P, Et₃N / acetonitrile / 6 h / 75 °C

4: 1.) diphenylphosphoryl azide, Et₃N / 1) toluene, reflux, 90 min; 2) toluene, reflux, 8 h, 45 deg C, 8 h

With n-butyllithium; diiodomethane; N,N,N,N,-tetramethylethylenediamine; diphenylphosphoranyl azide; palladium diacetate; triethylamine; triphenylphosphine; In acetonitrile;

DOI:10.1021/jo9605758

Reference yield:

(E)-3-[5-((E)-2-tert-Butoxycarbonylamino-vinyl)-9,9-dimethyl-9H-xanthen-4-yl]-acrylic acid ethyl ester (1026000-53-2) → 3-[5-(2-Amino-ethyl)-9,9-dimethyl-9H-xanthen-4-yl]-N-benzyl-propionamide (1026885-81-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 52 percent / H₂ / Pd/C / ethanol; acetic acid / 12 h / 1810.02 Torr

2: 92 percent / LiOH*H₂O / ethanol / 0 - 20 °C

3: (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, DIEA / CH₂Cl₂

4: TFA / CH₂Cl₂ / 0.83 h / Ambient temperature

With lithium hydroxide; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; acetic acid;

DOI:10.1021/jo9605758

Reference yield:

(E)-3-[5-((E)-2-tert-Butoxycarbonylamino-vinyl)-9,9-dimethyl-9H-xanthen-4-yl]-acrylic acid ethyl ester (1026000-53-2) → N-Benzyl-3-[9,9-dimethyl-5-(2-phenylacetylamino-ethyl)-9H-xanthen-4-yl]-propionamide

Guidance literature:

Multi-step reaction with 5 steps

1: 52 percent / H₂ / Pd/C / ethanol; acetic acid / 12 h / 1810.02 Torr

2: 92 percent / LiOH*H₂O / ethanol / 0 - 20 °C

3: (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, DIEA / CH₂Cl₂

4: TFA / CH₂Cl₂ / 0.83 h / Ambient temperature

5: (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, DIEA / CH₂Cl₂

With lithium hydroxide; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; acetic acid;

DOI:10.1021/jo9605758

upstream raw materials:

9,9-dimethylxanthene

Downstream raw materials:

3-[5-(2-Amino-ethyl)-9,9-dimethyl-9H-xanthen-4-yl]-N-benzyl-propionamide

{2-[5-(2-Benzylcarbamoyl-ethyl)-9,9-dimethyl-9H-xanthen-4-yl]-ethyl}-carbamic acid tert-butyl ester