Phenoxy acryloyl phosphoramidite, preparation method and application thereof
An alkoxy and alkyl technology, applied in the field of phenoxy acryloyl phosphite amides, can solve the problems of weak hydrophobicity, low synthesis yield, single category and the like
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Embodiment 1
[0058] Synthesis of Intermediate 1:
[0059]
[0060] Method A: At 0°C, add methacryloyl chloride (11.4g, 110mmol) dropwise to a round-bottomed flask containing a solution of 4-(2-aminoethyl)phenol (13.7g, 100mmol) in pyridine (100mL), Raised to room temperature for 2 hours. Saturated sodium bicarbonate solution was added to terminate the reaction, pyridine was distilled off under reduced pressure, and the obtained residue was subjected to column chromatography to obtain compound 1 (16.8 g, 82%) as a pale yellow solid.
[0061] Method B: Methacrylic acid (0.86 g, 10 mmol), 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC.HCL, 1.91 g, 10 mmol), N- Hydroxysuccinimide (NHS, 1.15 g, 10 mmol), 4-(2-aminoethyl)phenol, (1.37 g, 10 mmol) in dichloromethane (30 mL) was reacted at room temperature for 12 hours. The reaction solution was washed with aqueous sodium bicarbonate solution and saturated brine, the organic phase was dried over sodium sulfate, and the solven...
Embodiment 2
[0064] Synthesis of Intermediate 2:
[0065]
[0066] Method A: Add methacryloyl chloride (1.2 g, 11 mmol) dropwise to a round bottom flask containing a solution of 2-(4-iodophenyl)ethylamine (2.47 g, 10 mmol) in pyridine (10 mL) at 0°C , rise to room temperature and react for 5 hours. Saturated sodium bicarbonate solution was added to terminate the reaction, pyridine was distilled off under reduced pressure, and the obtained residue was subjected to column chromatography to obtain compound 2 (2.8 g, 89%) as a pale yellow solid.
[0067] 1 H NMR (400MHz, DMSO) δ9.20(s, 1H), 8.02(t, J=5.3Hz, 1H), 7.61(d, J=8.3Hz, 2H), 7.02(d, J=8.3Hz, 2H ), 5.63(s, 1H), 5.31(s, 1H), 3.24(dd, J=14.4, 6.3Hz, 2H), 2.66(t, J=7.2Hz, 2H), 1.83(s, 3H); 13 C NMR (101 MHz, DMSO) δ 167.09, 155.13, 137.41, 130.95, 130.13, 121.12, 115.32, 43.21, 36.32, 16.03. MS (ESI+): m / e = 316 (M+1).
Embodiment 3
[0069] Synthesis of Intermediate 3:
[0070]
[0071] Glycidol (6.5 g, 88 mmol), N-(4-hydroxyphenethyl)methacrylamide (16.4 g, 80 mmol) and triethylamine (8 mL) in ethanol (80 mL) were refluxed for 10 hours. The solvent was distilled off under reduced pressure, and the obtained residue was subjected to column chromatography to obtain compound 2 (17.6 g, 79%) as a white solid.
[0072] 1 H NMR (400MHz, DMSO) δ7.99(s, 1H), 7.10(d, J=8.4Hz, 2H), 6.85(d, J=8.4Hz, 2H), 5.61(s, 1H), 5.30(s , 1H), 4.95(d, J=4.7Hz, 1H), 4.68(t, J=5.6Hz, 1H), 3.95(dd, J=9.3, 3.7Hz, 1H), 3.83-3.75(m, 2H) , 3.43(t, J=5.4Hz, 2H), 3.27(dd, J=13.9, 6.7Hz, 2H), 2.68(t, J=7.4Hz, 2H), 1.83(s, 3H); 13 C NMR (101MHz, DMSO) δ 167.32, 157.11, 140.00, 131.27, 129.52, 118.80, 114.24, 69.91, 69.4562.68, 40.76, 34.16, 18.63. MS(ESI+): m / e=280(M+1) .
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