(S)-methyl 3-(3-bromo-4-methoxyphenyl)-2-((S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)propanoate

Base Information

• Chemical Name: (S)-methyl 3-(3-bromo-4-methoxyphenyl)-2-((S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)propanoate
• CAS No.: 98778-73-5
• Molecular Formula: C₂₅H₃₁BrN₂O₇
• Molecular Weight: 551.434
• Mol file: 98778-73-5.mol

Synonyms:(S)-methyl 3-(3-bromo-4-methoxyphenyl)-2-((S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)propanoate

Chemical Property of (S)-methyl 3-(3-bromo-4-methoxyphenyl)-2-((S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-methyl 3-(3-bromo-4-methoxyphenyl)-2-((S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)propanoate

There total 3 articles about (S)-methyl 3-(3-bromo-4-methoxyphenyl)-2-((S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)propanoate 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%

Boc-Tyr-OH (3978-80-1) + 3-bromo-4-O-methyl-L-tyrosine methyl ester hydrochloride (98778-84-8) → (S)-methyl 3-(3-bromo-4-methoxyphenyl)-2-((S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)propanoate (98778-73-5)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃; for 2h; Inert atmosphere;

DOI:10.1080/00397910903245166

Reference yield:

O-Methyltyrosine (6230-11-1) → (S)-methyl 3-(3-bromo-4-methoxyphenyl)-2-((S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)propanoate (98778-73-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Br₂, 98percent formic acid, 2.) 3N aq. HCl / 1.) 6 h, 2.) reflux, 1 h

2: 92 percent / thionyl chloride / 3 h / Heating

3: 87 percent / triethylamine, dicyclohexylcarbodiimide / dimethylformamide / 2 h / 0 °C

With hydrogenchloride; formic acid; thionyl chloride; bromine; triethylamine; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide;

DOI:10.1021/jo00224a051

Reference yield:

(S)-2-amino-3-(3-bromo-4-methoxyphenyl)propanoic acid (98778-82-6) → (S)-methyl 3-(3-bromo-4-methoxyphenyl)-2-((S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)propanoate (98778-73-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / thionyl chloride / 3 h / Heating

2: 87 percent / triethylamine, dicyclohexylcarbodiimide / dimethylformamide / 2 h / 0 °C

With thionyl chloride; triethylamine; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide;

DOI:10.1021/jo00224a051

upstream raw materials:

Boc-Tyr-OH

3-bromo-4-O-methyl-L-tyrosine methyl ester hydrochloride

O-Methyltyrosine

(S)-2-amino-3-(3-bromo-4-methoxyphenyl)propanoic acid

Downstream raw materials:

(S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)-3-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate

cyclo-3-bromo-4-O-methyl-L-tyrosyl-L-tyrosine