acetic acid 1-acetoxymethyl-2-(2-formylamino-5-iodo-4-pentyl-phenyl)-ethyl ester

Base Information

• Chemical Name: acetic acid 1-acetoxymethyl-2-(2-formylamino-5-iodo-4-pentyl-phenyl)-ethyl ester
• CAS No.: 442521-53-1
• Molecular Formula: C₁₉H₂₆INO₅
• Molecular Weight: 475.324

Synonyms:acetic acid 1-acetoxymethyl-2-(2-formylamino-5-iodo-4-pentyl-phenyl)-ethyl ester

Chemical Property of acetic acid 1-acetoxymethyl-2-(2-formylamino-5-iodo-4-pentyl-phenyl)-ethyl ester

Chemical Property:

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Technology Process of acetic acid 1-acetoxymethyl-2-(2-formylamino-5-iodo-4-pentyl-phenyl)-ethyl ester

There total 7 articles about acetic acid 1-acetoxymethyl-2-(2-formylamino-5-iodo-4-pentyl-phenyl)-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: 90.0%

formic acid (64-18-6) + acetic acid 1-acetoxymethyl-2-(2-amino-5-iodo-4-pentyl-phenyl)-ethyl ester (442521-52-0) → acetic acid 1-acetoxymethyl-2-(2-formylamino-5-iodo-4-pentyl-phenyl)-ethyl ester (442521-53-1)

Guidance literature:

formic acid; With acetic anhydride; at 50 ℃; for 2h;

acetic acid 1-acetoxymethyl-2-(2-amino-5-iodo-4-pentyl-phenyl)-ethyl ester; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4020(02)00099-6

Reference yield:

4-bromo-2-nitrotoluene (60956-26-5) → acetic acid 1-acetoxymethyl-2-(2-formylamino-5-iodo-4-pentyl-phenyl)-ethyl ester (442521-53-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 87.6 percent / tetrahydrofuran / 24 h / 40 °C

2.1: 73.5 percent / LiBH₄ / tetrahydrofuran / 1 h / 20 °C

3.1: 96.8 percent / pyridine / 0.5 h / 20 °C

4.1: 100 percent / PdCl₂(PPh₃)2; Et₃N; CuI / tetrahydrofuran / 18 h / 20 °C

5.1: 77.3 percent / H₂ / 10 percent Pd/C / ethanol / 20 °C / 760 Torr

6.1: 85.8 percent / benzyltrimethylammonium dichloroiodate; CaCO₃ / CH₂Cl₂ / 2.5 h / 20 °C

7.1: Ac₂O / 2 h / 50 °C

7.2: 90 percent / tetrahydrofuran / 0.5 h / 0 °C

With pyridine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; lithium borohydride; hydrogen; acetic anhydride; sodium hydride; N,N,N-trimethylbenzenemethanaminium dichloroiodate; triethylamine; calcium carbonate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; 4.1: Sonogashira coupling;

DOI:10.1016/S0040-4020(02)00099-6

Reference yield:

ethyl 3-(4-bromo-2-nitrophenyl)-2-oxopropanoate (442521-40-6) → acetic acid 1-acetoxymethyl-2-(2-formylamino-5-iodo-4-pentyl-phenyl)-ethyl ester (442521-53-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 73.5 percent / LiBH₄ / tetrahydrofuran / 1 h / 20 °C

2.1: 96.8 percent / pyridine / 0.5 h / 20 °C

3.1: 100 percent / PdCl₂(PPh₃)2; Et₃N; CuI / tetrahydrofuran / 18 h / 20 °C

4.1: 77.3 percent / H₂ / 10 percent Pd/C / ethanol / 20 °C / 760 Torr

5.1: 85.8 percent / benzyltrimethylammonium dichloroiodate; CaCO₃ / CH₂Cl₂ / 2.5 h / 20 °C

6.1: Ac₂O / 2 h / 50 °C

6.2: 90 percent / tetrahydrofuran / 0.5 h / 0 °C

With pyridine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; lithium borohydride; hydrogen; acetic anhydride; N,N,N-trimethylbenzenemethanaminium dichloroiodate; triethylamine; calcium carbonate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; 3.1: Sonogashira coupling;

DOI:10.1016/S0040-4020(02)00099-6

upstream raw materials:

formic acid

acetic acid 1-acetoxymethyl-2-(2-amino-5-iodo-4-pentyl-phenyl)-ethyl ester

4-bromo-2-nitrotoluene

ethyl 3-(4-bromo-2-nitrophenyl)-2-oxopropanoate

Downstream raw materials:

acetic acid 1-acetoxymethyl-2-(2-formylamino-4-pentyl-5-pent-1-ynyl-phenyl)-ethyl ester

2-({2-[3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-propyl]-4,5-dipentyl-phenyl}-methyl-amino)-hexanoic acid benzyl ester

acetic acid 1-acetoxymethyl-2-(2-formylamino-4,5-dipentyl-phenyl)-ethyl ester

3-(2-methylamino-4,5-dipentyl-phenyl)-propane-1,2-diol

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