(R)-2-TERT-BUTOXYCARBONYLAMINO-3-(2-FLUORO-4-HYDROXY-PHENYL)-PROPIONIC ACID

Base Information

• Chemical Name: (R)-2-TERT-BUTOXYCARBONYLAMINO-3-(2-FLUORO-4-HYDROXY-PHENYL)-PROPIONIC ACID
• CAS No.: 125218-32-8
• Molecular Formula: C14H18FNO5
• Molecular Weight: 299.2948232
• Mol file: 125218-32-8.mol

Synonyms:(R)-2-TERT-BUTOXYCARBONYLAMINO-3-(2-FLUORO-4-HYDROXY-PHENYL)-PROPIONIC ACID;N-BOC-2-FLUORO-D-TYROSINE

Chemical Property of (R)-2-TERT-BUTOXYCARBONYLAMINO-3-(2-FLUORO-4-HYDROXY-PHENYL)-PROPIONIC ACID

Chemical Property:

• Boiling Point: 488.1±45.0 °C(Predicted)
• PKA: 2.97±0.10(Predicted)
• PSA: 99.35000
• Density: 1.294±0.06 g/cm3(Predicted)
• LogP: 2.25610

Purity/Quality:

98% ^*data from raw suppliers

n-boc-2-fluoro-d-tyrosine 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-2-TERT-BUTOXYCARBONYLAMINO-3-(2-FLUORO-4-HYDROXY-PHENYL)-PROPIONIC ACID

There total 5 articles about (R)-2-TERT-BUTOXYCARBONYLAMINO-3-(2-FLUORO-4-HYDROXY-PHENYL)-PROPIONIC ACID 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: 84.0%

S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine (41840-28-2) + 2-fluoro-L-tyrosine (78709-81-6) → (S)-2-((tert-butoxycarbonyl)amino)-3-(2-fluoro-4-hydroxyphenyl)propanoic acid (N-Boc-2-fluorotyrosine) (125218-32-8)

Guidance literature:

DOI:10.1248/cpb.37.826

Reference yield:

(S)-2-amino-3-(2-fluoro-4-hydroxyphenyl)propionic acid hydrobromide (1131871-23-2) + di-tert-butyl dicarbonate (24424-99-5) → (S)-2-((tert-butoxycarbonyl)amino)-3-(2-fluoro-4-hydroxyphenyl)propanoic acid (N-Boc-2-fluorotyrosine) (125218-32-8)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; at 0 - 20 ℃; for 48h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + 2-fluoro-L-tyrosine (78709-81-6) → (S)-2-((tert-butoxycarbonyl)amino)-3-(2-fluoro-4-hydroxyphenyl)propanoic acid (N-Boc-2-fluorotyrosine) (125218-32-8)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; at 0 - 20 ℃;

DOI:10.1021/ja413174b

upstream raw materials:

S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine

2-fluoro-L-tyrosine

(S)-2-amino-3-(2-fluoro-4-hydroxyphenyl)propionic acid hydrobromide

di-tert-butyl dicarbonate

Downstream raw materials:

(S)-[2-((S)-2-carbamoylpyrrolidin-1-yl)-1-(2-fluoro-4-hydroxybenzyl)-2-oxoethyl]carbamic acid tert-butyl ester

(S)-2-((tert-butoxycarbonyl)amino)-3-(4-((tert-butyldimethylsilyl)oxy)-2-fluorophenyl)propanoic acid

{4-[2-amino-3-(2-fluoro-4-hydroxy-phenyl)-propionyl]-3-methoxycarbonylmethyl-2-oxo-piperazin-1-yl}-acetic acid

{1-[2-tert-butoxycarbonylamino-3-(2-fluoro-4-hydroxy-phenyl)-propionyl]-4-tert-butoxycarbonylmethyl-3-oxo-piperazin-2-yl}-acetic acid methyl ester

Refernces

• 1、 -. "COMPOUNDS FOR THE TREATMENT OF METABOLIC DISORDERS". Page/Page column 31-32. . Retrieved 2010/10/03.
• 2、 Maeda,Kawasaki,Watanabe,Kaneto. "Amino acids and peptides. X. Leu-enkephalin analogues containing a fluorinated aromatic amino acid". . p. 826 - 828. Retrieved 2007/10/02.