3-Bromo-L-phenylalanine Chemical Properties

Boiling point:

368.4±32.0 °C(Predicted)

Density 

1.588±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

2.16±0.10(Predicted)

form 

solid

color 

White to off white

optical activity

Consistent with structure

Water Solubility 

Slightly soluble in water.

Safety Information

HS Code 

2922498590

3-Bromo-L-phenylalanine Usage And Synthesis

Uses

3-Bromo-L-phenylalanine is used in preparation of lifitegrast intermediate.

Chemical Properties

White to off-white powder

Uses

It is applied in the facile removal of leader peptides from lanthipeptides by incorporation of a hydroxy acid.

Uses

3-Bromo-L-phenylalanine is used in preparation of lifitegrast intermediate.

Synthesis

The general procedure for the synthesis of (S)-2-amino-3-(3-bromophenyl)propionic acid from (S)-3-(3-bromophenyl)-2-((tert-butoxycarbonyl)amino)propionic acid was as follows: (S)-3-(3-bromophenyl)-2-((tert-butoxycarbonyl)amino)propionic acid (5.0 g, 14.5 mmol) was suspended in a 1,4-dioxane solution of 4 M hydrochloric acid (75 mL ) and the reaction was stirred at room temperature for 16 hours. Upon completion of the reaction, the white precipitate was collected by filtration and washed with ether (Et2O) to afford (S)-2-amino-3-(3-bromophenyl)propionic acid (3.2 g, 89% yield) as a white solid, and the product did not require further purification. The nuclear magnetic resonance hydrogen spectrum (1H NMR, CDCl3) data of the product were as follows: δ 8.32 (2H, s), 7.50-7.48 (2H, m), 7.34-7.29 (2H, m), 4.22 (1H, t, J=6.2 Hz), 3.13-3.11 (2H, m).

References

[1] Patent: WO2008/47109, 2008, A1. Location in patent: Page/Page column 42
[2] Patent: WO2006/114606, 2006, A1. Location in patent: Page/Page column 61

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