ChemicalBook CAS DataBase List BOC-3,5-DIIODO-L-TYROSINE

BOC-3,5-DIIODO-L-TYROSINE synthesis

4synthesis methods

Product Name:BOC-3,5-DIIODO-L-TYROSINE
CAS Number:62129-53-7
Molecular formula:C14H17I2NO5
Molecular Weight:533.1

24424-99-5 Synthesis

24424-99-5
833 suppliers
$13.50/25G

300-39-0 Synthesis

300-39-0
268 suppliers
$10.00/5g

62129-53-7
79 suppliers
$60.00/2g

Yield:-

Reaction Conditions:

with sodium hydrogencarbonate in methanol;water at 20;

Steps:

2 4.2 (S)-Methyl-2-(tert-butoxycarbonylamino)-3-(3,5-diiodo-4-methoxyphenyl)propanoate 17

l-Tyrosine 11 (5.14 g, 28.4 mmol) was dissolved in 73 mL of glacial AcOH and heated to 40 °C.
Then 3.2 mL of ICl in 23 mL of glacial AcOH was added dropwise to the reaction.
The mixture was heated at 80 °C for 8 h.
Then the solvent was evaporated and the residue was dissolved in MeOH/H₂O (2:1, 87 mL), and NaHCO₃ (8.3 g, 99.3 mmol), Boc₂O (7.3 mL, 34.1 mmol) were added.
The resulting mixture was stirred overnight at room temperature.
The solvent was evaporated and the residue was diluted with H₂O (60 mL), extracted with ethyl acetate (3*80 mL).
The combined organic layer was dried with Na₂SO₄, filtered, and the solvent evaporated in vacuo.
The crude was taken up in dry CH₃CN (142 mL) were added (CH₃)₂SO₄ (8.1 mL, 85.2 mmol) and anhydrous K₂CO₃ (11.8 g, 85.2 mmol), and the resulting mixture was stirred at 60 °C for 5 h.
The solvent removed in vacuo, and the water (150 mL) was added.
The mixture was extracted with ethyl acetate (3*100 mL).
The combined organic layer was dried with Na₂SO₄ and concentrated.
This crude product was purified over silica gel column chromatography to give the compound 17 as a pale yellow powder (11.5 g, 72% over three steps).
Mp 73-75 °C, [α]_D²⁶ +71 (c 1.1, in CHCl₃); IR(neat) ν_max: 3370, 2975, 1712, 1504, 1462, 1362, 1250, 1166, 1057, 996, 706 cm^-1; ¹H NMR (400 MHz, CDCl₃): δ (ppm) 7.47 (s, 2H), 5.19 (d, J=8 Hz, 1H), 4.42 (m, 1H), 3.74 (s, 3H), 3.67 (s, 3H), 2.98 (dd, J=5.4, 13.8 Hz, 1H), 2.81 (dd, J=6.7, 13.7 Hz, 1H), 1.35 (s, 9H); ¹³C NMR (100 MHz, CDCl₃): δ (ppm) 171.6, 157.6, 154.8, 140.4, 136.2, 90.3, 79.9, 60.5, 54.1, 52.4, 36.3, 28.2; HRMS (ESI⁺): m/z [M+Na]⁺ calcd for C₁₆H₂₁I₂NO₅Na: 583.9407; found: 583.9411.