N-Boc-tyramine Chemical Properties

Melting point:

71-75 °C

Boiling point:

395.7±25.0 °C(Predicted)

Density 

1.100±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

10.01±0.15(Predicted)

color 

Off-White to Pale Beige

InChI

InChI=1S/C13H19NO3/c1-13(2,3)17-12(16)14-9-8-10-4-6-11(15)7-5-10/h4-7,15H,8-9H2,1-3H3,(H,14,16)

InChIKey

ILNOTKMMDBWGOK-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NCCC1=CC=C(O)C=C1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HS Code 

2924.29.7790

N-Boc-tyramine Usage And Synthesis

Chemical Properties

White Solid

Uses

Intermediate in the preparation of Thyroxin derivatives.

Synthesis

a) Synthesis of N-(tert-butoxycarbonyl)-2-(4-hydroxyphenyl)ethylamine Tyramine hydrochloride (1.0 g, 5.76 mmol, 1 equiv.) was dissolved in a solvent mixture of dioxane and distilled water (25 mL/12 mL), followed by the addition of 10 mL of aqueous solution of NaOH (0.46 g, 11.5 mmol). After stirring for 10 min, di-tert-butyl dicarbonate (Boc2O) (1.26 g, 5.76 mmol, 1 equiv) was added. The reaction mixture was stirred overnight under argon protection and at room temperature. Upon completion of the reaction, dioxane was removed by evaporation and 40 mL of ethyl acetate (EtOAc) was added to the residual aqueous phase and the pH was adjusted to 7-8 with 1 M HCl solution.The organic and aqueous phases were separated, and the aqueous phase was extracted with EtOAc (2 x 15 mL). The organic phases were combined, dried with anhydrous Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (Al2O3, CH2Cl2/Hex, 85:15) to afford N-(tert-butoxycarbonyl)-2-(4-hydroxyphenyl)ethylamine (0.98 g, 73% yield). Melting point: 61-62°C. IR (KBr, cm-1): 3378.9 (-OH); 1686.6 (C=O). UV-Vis (CH2Cl2, λmax/nm): 277 (ε=1803). 1H-NMR (400 MHz, CDCl3): δ 1.441 (s, 9H, t-Bu); 2.703 (t, J=7.9 Hz, 2H, CH2CH2N); 3.329 (m, 2H, CH2CH2N); 4.602 (br s, 1H, NH or OH); 6.023 (br s, 1H, NH or OH); 6.774 (d, J=8.3 Hz, 2H, ArH); 7.013 (d, J=8.3 Hz, 2H, ArH). 13C-NMR (100 MHz, CDCl3): δ 28.84 (CMe3); 35.64 (CH2CH2N); 42.49 (CH2CH2N); 80.15 (CMe3); 115.97 (Cm); 130.18 (Ci); 130.50 (Cp); 155.38 (Cipso); 156.84 (C=O). Elemental analysis (C13H19NO3, calculated values): C, 65.80%; H, 8.07%; N, 5.90%; measured values: C, 65.77%; H, 8.09%; N, 5.90%. IE MS: m/z 181 [M-(Me)3CO-H+Na]+; 107 [M-(Me)3COC(O)NHCH2]+.

References

[1] Synthesis, 2009, # 22, p. 3838 - 3842
[2] Angewandte Chemie - International Edition, 2014, vol. 53, # 23, p. 5877 - 5881
[3] Angew. Chem., 2014, vol. 126, # 23, p. 5987 - 5991,5
[4] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 3, p. 633 - 639
[5] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 15, p. 5496 - 5509

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