BOC-L-3-FLUOROPHENYLALANINE Chemical Properties

Melting point:

75-80 °C

Boiling point:

425.0±40.0 °C(Predicted)

Density 

1.1918 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

slightly sol. in Ethanol

form 

powder to crystal

pka

3.82±0.10(Predicted)

color 

White to Almost white

optical activity

[α]20/D +6.5±1°, c = 1% in methanol

BRN 

5347375

InChI

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

InChIKey

FPCCREICRYPTTL-NSHDSACASA-N

SMILES

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

CAS DataBase Reference

114873-01-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

HazardClass 

IRRITANT

HS Code 

2922498590

MSDS

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

BOC-L-3-FLUOROPHENYLALANINE Usage And Synthesis

Chemical Properties

off-white crystalline powder

Uses

peptide synthesis

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

The general procedure for the synthesis of (S)-2-((tert-butoxycarbonyl)amino)-3-(3-fluorophenyl)propionic acid from di-tert-butyl dicarbonate and L-3-fluorophenylalanine was as follows: first, L-2-amino-3-(3-fluorophenyl)-propionic acid (20.0 g, 110 mmol, 1 eq.) was dissolved in water (100 mL) and sodium carbonate (16.2 g. 153 mmol, 1.4 eq.) in water (40 mL). Subsequently, 1,4-dioxane (100 mL) was added and the mixture was cooled to 0 °C. Di-tert-butyl dicarbonate was added with stirring and the reaction mixture was then stirred at room temperature for 5 hours. After the reaction was complete, the dioxane was removed by evaporation. Water (125 mL) was added to dilute the reaction mixture, which was subsequently washed with ether (2 x 100 mL). The aqueous phase was acidified with 10% citric acid and then extracted with ethyl acetate (2 x 300 mL). The organic phases were combined, washed sequentially with water (2×150 mL) and brine (150 mL), dried with anhydrous sodium sulfate, and concentrated to afford the target product (S)-2-((tert-butoxycarbonyl)amino)-3-(3-fluorophenyl)propionic acid as a colorless viscous oil, which slowly solidified after standing (31 g, quantitative yield). The 1H NMR (CDCl3) data of the product were as follows: δ 7.33-7.26 (m, 1H), 7.00-6.91 (m, 3H), 4.96 (s, 1H), 4.62 (bs, 1H), 3.23 (dd, J = 14, 5.3Hz, 2H), 1.44 (s, 9H). Elemental analysis (C14H18NO4F) calculated values: C, 59.36; H, 6.40; N, 4.94. measured values: C, 59.29; H, 6.34; N, 4.90.

References

[1] Patent: WO2005/26114, 2005, A1. Location in patent: Page/Page column 85
[2] Patent: WO2005/26114, 2005, A1. Location in patent: Page/Page column 102
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 13, p. 2090 - 2099

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