2-(S)-[2-(S)-{2-(S)-tert-butoxycarbonylamino-3-[4-(5-iodo-2-methoxyphenoxy)phenyl]propionylamino}-3-(4-methoxyphenyl)-propionylamino]-3-hydroxypropionic acid methyl ester

Base Information

• Chemical Name: 2-(S)-[2-(S)-{2-(S)-tert-butoxycarbonylamino-3-[4-(5-iodo-2-methoxyphenoxy)phenyl]propionylamino}-3-(4-methoxyphenyl)-propionylamino]-3-hydroxypropionic acid methyl ester
• CAS No.: 327621-04-5
• Molecular Formula: C₃₅H₄₂IN₃O₁₀
• Molecular Weight: 791.637

Synonyms:2-(S)-[2-(S)-{2-(S)-tert-butoxycarbonylamino-3-[4-(5-iodo-2-methoxyphenoxy)phenyl]propionylamino}-3-(4-methoxyphenyl)-propionylamino]-3-hydroxypropionic acid methyl ester

Chemical Property of 2-(S)-[2-(S)-{2-(S)-tert-butoxycarbonylamino-3-[4-(5-iodo-2-methoxyphenoxy)phenyl]propionylamino}-3-(4-methoxyphenyl)-propionylamino]-3-hydroxypropionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(S)-[2-(S)-{2-(S)-tert-butoxycarbonylamino-3-[4-(5-iodo-2-methoxyphenoxy)phenyl]propionylamino}-3-(4-methoxyphenyl)-propionylamino]-3-hydroxypropionic acid methyl ester

There total 8 articles about 2-(S)-[2-(S)-{2-(S)-tert-butoxycarbonylamino-3-[4-(5-iodo-2-methoxyphenoxy)phenyl]propionylamino}-3-(4-methoxyphenyl)-propionylamino]-3-hydroxypropionic acid methyl 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: 94.0%

2-(S)-tert-butoxycarbonylamino-3-[4-(5-iodo-2-methoxyphenoxy)phenyl]propionic acid (327621-00-1) + H-Tyr(OMe)-Ser-OMe hydrochloride → 2-(S)-[2-(S)-{2-(S)-tert-butoxycarbonylamino-3-[4-(5-iodo-2-methoxyphenoxy)phenyl]propionylamino}-3-(4-methoxyphenyl)-propionylamino]-3-hydroxypropionic acid methyl ester (327621-04-5)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1039/b008078k

Reference yield:

Boc-Tyr-OH (3978-80-1) → 2-(S)-[2-(S)-{2-(S)-tert-butoxycarbonylamino-3-[4-(5-iodo-2-methoxyphenoxy)phenyl]propionylamino}-3-(4-methoxyphenyl)-propionylamino]-3-hydroxypropionic acid methyl ester (327621-04-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: K₂CO₃ / dimethylformamide / 96 h / 70 °C

2.1: NaHCO₃ / dimethylformamide / 16 h / 20 °C

3.1: MCPBA; NaHCO₃ / CHCl₃ / 16 h / 55 °C

4.1: K₂CO₃; MeOH

5.1: Chloramine-T hydrate; NaI / dimethylformamide / 1.5 h / 20 °C

5.2: K₂CO₃ / dimethylformamide / 16 h / 20 °C

6.1: 100 percent / aq. LiOH / tetrahydrofuran

7.1: 94 percent / EDCI; iPr₂NEt; BtOH / dimethylformamide / 16 h / 20 °C

With methanol; lithium hydroxide; chloroamine-T; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide; 3.1: Perkin reaction;

DOI:10.1039/b008078k

Reference yield:

2-Fluorobenzaldehyde (446-52-6) → 2-(S)-[2-(S)-{2-(S)-tert-butoxycarbonylamino-3-[4-(5-iodo-2-methoxyphenoxy)phenyl]propionylamino}-3-(4-methoxyphenyl)-propionylamino]-3-hydroxypropionic acid methyl ester (327621-04-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: K₂CO₃ / dimethylformamide / 96 h / 70 °C

2.1: NaHCO₃ / dimethylformamide / 16 h / 20 °C

3.1: MCPBA; NaHCO₃ / CHCl₃ / 16 h / 55 °C

4.1: K₂CO₃; MeOH

5.1: Chloramine-T hydrate; NaI / dimethylformamide / 1.5 h / 20 °C

5.2: K₂CO₃ / dimethylformamide / 16 h / 20 °C

6.1: 100 percent / aq. LiOH / tetrahydrofuran

7.1: 94 percent / EDCI; iPr₂NEt; BtOH / dimethylformamide / 16 h / 20 °C

With methanol; lithium hydroxide; chloroamine-T; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide; 3.1: Perkin reaction;

DOI:10.1039/b008078k

upstream raw materials:

2-(S)-tert-butoxycarbonylamino-3-[4-(5-iodo-2-methoxyphenoxy)phenyl]propionic acid

Boc-Tyr-OH

2-Fluorobenzaldehyde

2-(S)-tert-butoxycarbonylamino-3-[4-(2-hydroxyphenoxy)phenyl]propionic acid methyl ester

Downstream raw materials:

15-(S)-tert-butoxycarbonylamino-4-methoxy-12-(S)-(4-methoxybenzyl)-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.1(3,7)]-docosa-1-⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-(S)-carboxylic acid methyl ester

(9S,12S,15S)-15-Acetylamino-4-methoxy-12-(4-methoxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-carboxylic acid methyl ester

K-13

2-(R)-[2-(S)-{2-(S)-tert-butoxycarbonylamino-3-[4-(5-iodo-2-methoxyphenoxy)phenyl]propionylamino}-3-(4-methoxyphenyl)-propionylamino]-3-iodopropionic acid methyl ester

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