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

Base Information

• Chemical Name: {2-[5-(2-Benzylcarbamoyl-ethyl)-9,9-dimethyl-9H-xanthen-4-yl]-ethyl}-carbamic acid tert-butyl ester
• CAS No.: 182153-49-7
• Molecular Formula: C₃₂H₃₈N₂O₄
• Molecular Weight: 514.665
• Mol file: 182153-49-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about {2-[5-(2-Benzylcarbamoyl-ethyl)-9,9-dimethyl-9H-xanthen-4-yl]-ethyl}-carbamic acid tert-butyl 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) → {2-[5-(2-Benzylcarbamoyl-ethyl)-9,9-dimethyl-9H-xanthen-4-yl]-ethyl}-carbamic acid tert-butyl ester (182153-49-7)

Guidance literature:

Multi-step reaction with 7 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

5: 52 percent / H₂ / Pd/C / ethanol; acetic acid / 12 h / 1810.02 Torr

6: 92 percent / LiOH*H₂O / ethanol / 0 - 20 °C

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

With lithium hydroxide; n-butyllithium; diiodomethane; N,N,N,N,-tetramethylethylenediamine; diphenylphosphoranyl azide; hydrogen; palladium diacetate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium on activated charcoal; In ethanol; dichloromethane; acetic acid; acetonitrile;

DOI:10.1021/jo9605758

Reference yield:

?4,5-diiodo-9,9-dimethylxanthene (182153-21-5) → {2-[5-(2-Benzylcarbamoyl-ethyl)-9,9-dimethyl-9H-xanthen-4-yl]-ethyl}-carbamic acid tert-butyl ester (182153-49-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 24 percent / palladium acetate, Ph₃P, Et₃N / acetonitrile / 6 h / 75 °C

2: 63 percent / palladium acetate, Ph₃P, Et₃N / acetonitrile / 6 h / 75 °C

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

4: 52 percent / H₂ / Pd/C / ethanol; acetic acid / 12 h / 1810.02 Torr

5: 92 percent / LiOH*H₂O / ethanol / 0 - 20 °C

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

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

DOI:10.1021/jo9605758

Reference yield:

(E)-3-(5-Iodo-9,9-dimethyl-9H-xanthen-4-yl)-acrylic acid ethyl ester → {2-[5-(2-Benzylcarbamoyl-ethyl)-9,9-dimethyl-9H-xanthen-4-yl]-ethyl}-carbamic acid tert-butyl ester (182153-49-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 63 percent / palladium acetate, Ph₃P, Et₃N / acetonitrile / 6 h / 75 °C

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

3: 52 percent / H₂ / Pd/C / ethanol; acetic acid / 12 h / 1810.02 Torr

4: 92 percent / LiOH*H₂O / ethanol / 0 - 20 °C

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

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

DOI:10.1021/jo9605758

upstream raw materials:

benzylamine

3-[5-(2-tert-Butoxycarbonylamino-ethyl)-9,9-dimethyl-9H-xanthen-4-yl]-propionic acid

9,9-dimethylxanthene

?4,5-diiodo-9,9-dimethylxanthene

Downstream raw materials:

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