(S)-2-TERT-BUTOXYCARBONYLAMINO-3-(4-FLUORO-PHENYL)-PROPIONIC ACID METHYL ESTER

Base Information

• Chemical Name: (S)-2-TERT-BUTOXYCARBONYLAMINO-3-(4-FLUORO-PHENYL)-PROPIONIC ACID METHYL ESTER
• CAS No.: 134362-34-8
• Molecular Formula: C₁₅H₂₀FNO₄
• Molecular Weight: 297.327
• Mol file: 134362-34-8.mol

Synonyms:methyl 2-(S)-((tert-butoxycarbonyl)amino)-3-(4'-fluorophenyl)propanoate

Chemical Property of (S)-2-TERT-BUTOXYCARBONYLAMINO-3-(4-FLUORO-PHENYL)-PROPIONIC ACID METHYL ESTER

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

(S)-2-TERT-BUTOXYCARBONYLAMINO-3-(4-FLUORO-PHENYL)-PROPIONIC ACID METHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-TERT-BUTOXYCARBONYLAMINO-3-(4-FLUORO-PHENYL)-PROPIONIC ACID METHYL ESTER

There total 11 articles about (S)-2-TERT-BUTOXYCARBONYLAMINO-3-(4-FLUORO-PHENYL)-PROPIONIC 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: 87.0%

methanol (67-56-1) + Boc-Phe(p-F) (41153-30-4,57292-45-2,79561-25-4,129101-25-3) → methyl 2-(S)-((tert-butoxycarbonyl)amino)-3-(4'-fluorophenyl)propanoate (134362-34-8,86129-35-3)

Guidance literature:

Boc-Phe(p-F); With triethylamine; isobutyl chloroformate; In dichloromethane; at 0 ℃;

methanol; In dichloromethane; for 0.5h;

Reference yield: 85.0%

N-tert-butoxycarbonyl-4-(tri-n-butylstannyl)-L-phenylalanine methyl ester (151842-29-4) → methyl 2-(S)-((tert-butoxycarbonyl)amino)-3-(4'-fluorophenyl)propanoate (134362-34-8,86129-35-3)

Guidance literature:

With sodium triflate; sodium hydrogencarbonate; 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(hexafluorophosphate); silver(l) oxide; In acetone; at 23 - 65 ℃;

Reference yield: 80.0%

4-fluoro-1-iodobenzene (352-34-1) + N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester (93267-04-0,170848-34-7,889670-02-4) → methyl 2-(S)-((tert-butoxycarbonyl)amino)-3-(4'-fluorophenyl)propanoate (134362-34-8,86129-35-3)

Guidance literature:

N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester; With iodine; zinc; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

4-fluoro-1-iodobenzene; With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.1021/jo902238n

upstream raw materials:

4-fluoro-1-iodobenzene

N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester

1-Bromo-4-fluorobenzene

methyl 2-[(tert-butoxycarbonyl)amino]acrylate

Downstream raw materials:

(S)-tert-butyl 4-(diethoxyphosphoryl)-1-(4-fluorophenyl)-3-oxobutan-2-ylcarbamate

methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate

methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-fluoro-3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate

Refernces

• 1、 Key, Hanna M.,Miller, Scott J.. "Site- and Stereoselective Chemical Editing of Thiostrepton by Rh-Catalyzed Conjugate Arylation: New Analogues and Collateral Enantioselective Synthesis of Amino Acids". . p. 15460 - 15466. Retrieved 2017/11/06.
• 2、 Ross, Andrew J.,Lang, Hannah L.,Jackson, Richard F. W.. "Much improved conditions for the Negishi cross-coupling of iodoalanine derived zinc reagents with aryl halides". supporting information; experimental part. p. 245 - 248. Retrieved 2010/04/06.