methyl 2-{4-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-oxo-3-(pentylamino)propyl]-2-iodophenoxy}acetate

Base Information

• Chemical Name: methyl 2-{4-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-oxo-3-(pentylamino)propyl]-2-iodophenoxy}acetate
• CAS No.: 292835-93-9
• Molecular Formula: C₂₂H₃₃IN₂O₆
• Molecular Weight: 548.418
• Mol file: 292835-93-9.mol

Synonyms:methyl 2-{4-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-oxo-3-(pentylamino)propyl]-2-iodophenoxy}acetate

Chemical Property of methyl 2-{4-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-oxo-3-(pentylamino)propyl]-2-iodophenoxy}acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-{4-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-oxo-3-(pentylamino)propyl]-2-iodophenoxy}acetate

There total 1 articles about methyl 2-{4-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-oxo-3-(pentylamino)propyl]-2-iodophenoxy}acetate 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: 89.0%

bromoacetic acid methyl ester (96-32-2) + tert-butyl (1S)-1-(4-hydroxy-3-iodobenzyl)-2-oxo-2-(pentylamino)ethylcarbamate (221077-42-5) → methyl 2-{4-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-oxo-3-(pentylamino)propyl]-2-iodophenoxy}acetate (292835-93-9)

Guidance literature:

With potassium carbonate; In acetone; at 50 ℃;

DOI:10.1021/jm011100y

Reference yield: 47.0%

propynoic acid ethyl ester (623-47-2) + methyl 2-{4-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-oxo-3-(pentylamino)propyl]-2-iodophenoxy}acetate (292835-93-9) → ethyl 3-[5-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-oxo-3-(pentylamino)propyl]-2-(2-methoxy-2-oxoethoxy)phenyl]-2-propynoate (292835-94-0)

Guidance literature:

With copper(I) oxide; In N,N-dimethyl-formamide; at 110 ℃; for 16h;

DOI:10.1021/jm011100y

Reference yield:

methyl 2-{4-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-oxo-3-(pentylamino)propyl]-2-iodophenoxy}acetate (292835-93-9) → 3-{5-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-2-pentylcarbamoyl-ethyl]-2-carboxymethoxy-phenyl}-propionic acid

Guidance literature:

Multi-step reaction with 5 steps

1: 47 percent / Cu₂O / dimethylformamide / 16 h / 110 °C

2: TFA / CH₂Cl₂ / 4 h / 0 - 20 °C

3: 1.09 g / 1-hydroxybenzotriazole; EDC / CH₂Cl₂ / 20 °C

4: 99 percent / 2.5 M aq. LiOH / tetrahydrofuran / 4.5 h / 20 °C

5: 98 percent / H₂ / 10percent Pd/C / methanol / 4 h / atmospheric pressure

With copper(I) oxide; lithium hydroxide; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; 10percent Pd/C; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm011100y

upstream raw materials:

bromoacetic acid methyl ester

tert-butyl (1S)-1-(4-hydroxy-3-iodobenzyl)-2-oxo-2-(pentylamino)ethylcarbamate

Downstream raw materials:

ethyl 3-[5-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-oxo-3-(pentylamino)propyl]-2-(2-methoxy-2-oxoethoxy)phenyl]-2-propynoate

{5-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-2-pentylcarbamoyl-ethyl]-2-carboxymethoxy-phenyl}-propynoic acid

ethyl 3-[5-[(2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-oxo-3-(pentylamino)propyl]-2-(2-methoxy-2-oxoethoxy)phenyl]-2-propynoate