BOC-L-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.

form 

Powder

pka

3.87±0.10(Predicted)

color 

White

optical activity

8.8°(C=1.00g/100ml MEOH)

BRN 

4323475

InChI

InChI=1S/C14H18FNO4/c1-14(2,3)20-13(19)16-11(12(17)18)8-9-4-6-10(15)7-5-9/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m0/s1

InChIKey

RCXSXRAUMLKRRL-NSHDSACASA-N

SMILES

C(O)(=O)[C@H](CC1=CC=C(F)C=C1)NC(OC(C)(C)C)=O

CAS DataBase Reference

41153-30-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

HS Code 

29242990

MSDS

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

BOC-L-4-Fluorophe Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

Boc-Phe(4-F)-OH, 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.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

General procedure for the synthesis of Boc-L-4-fluorophenylalanine from di-tert-butyl dicarbonate and (S)-2-amino-3-(4-fluorophenyl)propionic acid: (S)-2-amino-3-(4-fluorophenyl)propionic acid (1.97 g, 10 mmol) was dissolved in a mixture of dioxane (20 mL), water (20 mL), and 1 M NaOH (10 mL), stirred and cooled in an ice water bath. Di-tert-butyl dicarbonate (2.4 g, 11 mmol) was added slowly and the reaction mixture was continued to be stirred for 6 hours at room temperature. Upon completion of the reaction, the solution was concentrated under reduced pressure to about 15-20 mL and then cooled in an ice water bath. The concentrate was covered with ethyl acetate (~30 mL) and acidified to pH 2-3 with the addition of dilute KHSO4 solution. the aqueous phase was separated and extracted three times with ethyl acetate. The organic phases were combined, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure to give a waxy solid product. Yield: 2.115 g (7.25 mmol, 72.5% yield). The product was characterized by 1H NMR and MALDI-TOF mass spectrometry: 1H NMR (DMSO-d6, 400 MHz, ppm): 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), 3.03-2.77 ( m, 2H, CH2), 1.33 (s, 9H, Boc). MALDI-TOF (Substrate: α-cyano-4-hydroxycinnamic acid (CHCA)): m/z = [M + H]+ 284.12 (calculated), 284.29 (observed), [M + Na]+ 306.11 (calculated), 306.25 (observed).

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-L-4-Fluorophe (41153-30-4)Related Product Information

• N-(tert-Butoxycarbonyl)-L-phenylalanine
• N-Carbobenzyloxyglycine
• EC 2.6.1.2
• tert-Butanol
• D-Phenylalanine
• DL-Phenylalanine
• Phenprobamate
• Boc-Aib-OH
• D-Alanine
• BOC-L-3,4-Difluorophe
• BOC-D-3-FLUOROPHE
• BOC-L-2-FLUOROPHE
• BOC-L-4-Methylphe
• L-Phenylalanine
• BOC-GLY-LEU-OH
• BOC-L-PENTAFLUOROPHENYLALANINE
• (S)-N-Boc-(4-Pyridyl)alanine
• BOC-L-4-Chlorophe