L-Phenylalanine, 4-bromo-N-[(1,1-dimethylethoxy)carbonyl]-, ethyl ester

Base Information

• Chemical Name: L-Phenylalanine, 4-bromo-N-[(1,1-dimethylethoxy)carbonyl]-, ethyl ester
• CAS No.: 591249-54-6
• Molecular Formula: C16H22BrNO4
• Molecular Weight: 372.259

Synonyms:N-Boc-4-bromo-L-phenylalanine ethyl ester;ethyl (αS)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-4-bromobenzene;

Chemical Property of L-Phenylalanine, 4-bromo-N-[(1,1-dimethylethoxy)carbonyl]-, ethyl ester

Chemical Property:

• PSA: 64.63000
• LogP: 3.83890

Purity/Quality:

99% ^*data from raw suppliers

N-Boc-4-bromo-L-phenylalanine ethyl ester 95+% ee ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Phenylalanine, 4-bromo-N-[(1,1-dimethylethoxy)carbonyl]-, ethyl ester

There total 1 articles about L-Phenylalanine, 4-bromo-N-[(1,1-dimethylethoxy)carbonyl]-, 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: 76.0%

ethyl iodide (75-03-6) + 4-bromo-N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalanine (62129-39-9,79561-82-3) → ethyl (S)-3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoate (591249-54-6,1047975-40-5)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1002/anie.201602908

Reference yield: 57.0%

ethyl (S)-3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoate (591249-54-6,1047975-40-5) + 1-(phenylsulfonyl)-1H-indol-3-ylboronic acid (129271-98-3) → ethyl N-(tert-butoxycarbonyl)-4-[1-(phenylsulfonyl)-1H-indol-3-yl]-L-phenylalaninate (1031342-07-0)

Guidance literature:

With potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In water; at 90 ℃; for 20h;

Reference yield:

ethyl (S)-3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoate (591249-54-6,1047975-40-5) → (S)-2-((tert-butoxycarbonyl)amino)-3-(4-(3,5-dimethylisoxazol-4-yl)phenyl)propanoicacid

Guidance literature:

Multi-step reaction with 2 steps

1: palladium diacetate; ruphos; sodium carbonate / ethanol / 24 h / 100 °C / Sealed tube; Inert atmosphere

2: lithium hydroxide / water; methanol; tetrahydrofuran

With palladium diacetate; sodium carbonate; lithium hydroxide; ruphos; In tetrahydrofuran; methanol; ethanol; water;

DOI:10.1002/anie.201602908

upstream raw materials:

ethyl iodide

4-bromo-N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalanine

Downstream raw materials:

ethyl N-(tert-butoxycarbonyl)-4-[1-(phenylsulfonyl)-1H-indol-3-yl]-L-phenylalaninate

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