5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxane-5-carboxylic acid 2-(4-iodo-phenyl)-2-oxo-ethyl ester

Base Information

• Chemical Name: 5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxane-5-carboxylic acid 2-(4-iodo-phenyl)-2-oxo-ethyl ester
• CAS No.: 863483-01-6
• Molecular Formula: C₂₀H₂₆INO₇
• Molecular Weight: 519.333
• Mol file: 863483-01-6.mol

Synonyms:5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxane-5-carboxylic acid 2-(4-iodo-phenyl)-2-oxo-ethyl ester

Chemical Property of 5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxane-5-carboxylic acid 2-(4-iodo-phenyl)-2-oxo-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxane-5-carboxylic acid 2-(4-iodo-phenyl)-2-oxo-ethyl ester

There total 5 articles about 5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxane-5-carboxylic acid 2-(4-iodo-phenyl)-2-oxo-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: 86.0%

5-((tertbutoxycarbonyl)amino)-2,2-dimethyl-1,3-dioxane-5-carboxylic acid (654067-56-8) + 2-bromo-1-(4-iodophenyl)ethanone (31827-94-8) → 5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxane-5-carboxylic acid 2-(4-iodo-phenyl)-2-oxo-ethyl ester (863483-01-6)

Guidance literature:

5-((tertbutoxycarbonyl)amino)-2,2-dimethyl-1,3-dioxane-5-carboxylic acid; With caesium carbonate; In ethanol; at 20 ℃; for 1h;

2-bromo-1-(4-iodophenyl)ethanone; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2005.05.097

Reference yield:

(5-amino-2,2-dimethyl-1,3-dioxan-5-yl)methanol (53104-32-8) → 5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxane-5-carboxylic acid 2-(4-iodo-phenyl)-2-oxo-ethyl ester (863483-01-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: aq. NaHCO₃ / tetrahydrofuran / 12 h / 20 °C

2.1: 74 percent / (COCl)2; TEA; DMSO / CH₂Cl₂ / 2 h / -78 - 20 °C

3.1: 95 percent / NaClO₂; aq. NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 20 °C

4.1: Cs₂CO₃ / ethanol / 1 h / 20 °C

4.2: 86 percent / dimethylformamide / 1 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; TEA; sodium hydrogencarbonate; caesium carbonate; dimethyl sulfoxide; In tetrahydrofuran; ethanol; dichloromethane; tert-butyl alcohol; 2.1: Swern oxidation;

DOI:10.1016/j.bmcl.2005.05.097

Reference yield:

4-Iodoacetophenone (13329-40-3) → 5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxane-5-carboxylic acid 2-(4-iodo-phenyl)-2-oxo-ethyl ester (863483-01-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 65 percent / Br₂ / diethyl ether; dioxane / 12 h / 20 °C

2.1: Cs₂CO₃ / ethanol / 1 h / 20 °C

2.2: 86 percent / dimethylformamide / 1 h / 20 °C

With bromine; caesium carbonate; In 1,4-dioxane; diethyl ether; ethanol;

DOI:10.1016/j.bmcl.2005.05.097

upstream raw materials:

5-((tertbutoxycarbonyl)amino)-2,2-dimethyl-1,3-dioxane-5-carboxylic acid

2-bromo-1-(4-iodophenyl)ethanone

(5-amino-2,2-dimethyl-1,3-dioxan-5-yl)methanol

4-Iodoacetophenone

Downstream raw materials:

{2,2-dimethyl-5-[5-(4-oct-1-ynyl-phenyl)-1H-imidazol-2-yl]-[1,3]dioxan-5-yl}-carbamic acid tert-butyl ester

{2,2-dimethyl-5-[5-(4-octyl-phenyl)-1H-imidazol-2-yl]-[1,3]dioxan-5-yl}-carbamic acid tert-butyl ester

{5-[5-(4-iodo-phenyl)-1H-imidazol-2-yl]-2,2-dimethyl-[1,3]dioxan-5-yl}-carbamic acid tert-butyl ester