BOC-3,5-DIIODO-L-TYROSINE synthesis
- Product Name:BOC-3,5-DIIODO-L-TYROSINE
- CAS Number:62129-53-7
- Molecular formula:C14H17I2NO5
- Molecular Weight:533.1
24424-99-5
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300-39-0
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62129-53-7
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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) νmax: 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.
References:
Chen, Ruijiao;Liu, Hao;Liu, Xiubing;Chen, Xiaochuan [Tetrahedron,2013,vol. 69,# 17,p. 3565 - 3570]
128781-80-6
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62129-53-7
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60-18-4
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62129-53-7
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