| Identification | Back Directory | [Name]
N-Boc-tyramine | [CAS]
64318-28-1 | [Synonyms]
64318-28-1
BOC-TYRAMINE
Zinc02563753
N-Boc-tyramine
N-Boc-4-hydroxyphenethylamine
N-(tert-Butoxycarbonyl)tyramine
N-Boc-2-(4-hydroxyphenyl)ethylamine
N-(tert-Butoxycarbonyl)tyramine >
tert-Butyl 4-hydroxyphenethylcarbaMate
4-[2-(N-tert-ButoxycarbonylaMino)ethyl]phenol
tert-Butyl [2-(4-Hydroxyphenyl)ethyl]carbamate
N-(tert-Butoxycarbonyl)-4-hydroxyphenethylamine
tert-butyl N-[2-(4-hydroxyphenyl)ethyl]carbamate
[2-(4-HYDROXY-PHENYL)-ETHYL]-CARBAMIC ACID TERT-BUTYL ESTER
N-[2-(4-Hydroxyphenyl)ethyl]carbaMic Acid 1,1-DiMethylethyl Ester
Carbamic acid, N-[2-(4-hydroxyphenyl)ethyl]-, 1,1-dimethylethyl ester
N-Boc-tyramine
N-(tert-Butoxycarbonyl)-4-hydroxyphenethylamine
N-Boc-4-hydroxyphenethylamine | [Molecular Formula]
C13H19NO3 | [MDL Number]
MFCD05864730 | [MOL File]
64318-28-1.mol | [Molecular Weight]
237.29 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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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