BOC-D-4-Fluorophe Chemical Properties

Melting point:

83-86 °C

alpha 

-8 º (c=1,MeOH)

Boiling point:

431.2±40.0 °C(Predicted)

Density 

1.1918 (estimate)

storage temp. 

Sealed in dry,2-8°C

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

pka

3.87±0.10(Predicted)

form 

powder to crystal

color 

White to Almost white

CAS DataBase Reference

57292-45-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-24/25

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

HS Code 

29242990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

BOC-D-4-Fluorophe Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

Boc-D-4-Fluorophenylalanine, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

Synthesis

GENERAL STEPS: (S)-2-Amino-3-(4-fluorophenyl)propanoic acid (1.97 g, 10 mmol) was dissolved in a mixture of dioxane (20 mL), water (20 mL) and 1M NaOH (10 mL), stirred and cooled in an ice water bath. Di-tert-butyl dicarbonate (2.4 g, 11 mmol) was added to the reaction system, followed by continued stirring for 6 hours at room temperature. Upon completion of the reaction, the solution was concentrated under vacuum to about 15-20 mL and again cooled in an ice water bath. The concentrate was covered with ethyl acetate (~30 mL) and acidified to pH 2-3 by adding dilute KHSO4 solution. the aqueous phase was separated and extracted three times with ethyl acetate. The ethyl acetate extracts were combined and dried over anhydrous Na2SO4 followed by vacuum evaporation of the solvent. The resulting product was a waxy solid with a yield of 2.115 g (7.25 mmol, 72.5% yield). The product was characterized by 1H NMR (DMSO-d6, 400 MHz) and MALDI-TOF mass spectrometry.1H NMR data: δ 12.60 (s, 1H, COOH), 7.29-7.25 and 7.11-7.07 (m, 4H, aromatic protons), 4.10-3.00 (m, 1H, CH-4F-Phe), 3.03- 2.77 (m, 2H, CH2-4F-Phe), 1.33 (s, 9H, Boc).MALDI-TOF mass spectrometry data (matrix: α-cyano-4-hydroxycinnamic acid (CHCA)): m/z [M + H]+ 284.12 (calculated), 284.29 (observed); [M + Na]+ 306.11 (calculated), 306.25 (calculated). 306.25 (observed value).

References

[1] Chemical Communications, 2014, vol. 50, # 76, p. 11154 - 11157
[2] Patent: WO2017/42805, 2017, A1. Location in patent: Page/Page column 24; 25
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 13, p. 2090 - 2099
[4] Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 10, p. 1733 - 1745

BOC-D-4-Fluorophe (57292-45-2)Related Product Information

• D-Phenylalanine
• D-Alanine
• DL-Phenylalanine
• N-(tert-Butoxycarbonyl)-L-phenylalanine
• tert-Butanol
• N-Carbobenzyloxyglycine
• Phenprobamate
• Boc-Aib-OH
• EC 2.6.1.2
• L-Phenylalanine
• BOC-GLY-LEU-OH
• BOC-D-4-Fluorophe
• Fluorine
• BOC-D-3,4-Difluorophe
• BOC-L-3-FLUOROPHE
• BOC-D-2-FLUOROPHE
• BOC-D-3-FLUOROPHE
• BOC-L-2-FLUOROPHE