Synthesis methods of sunset yellow hapten and artificial antigen
A synthesis method, technology of sunset yellow, applied in chemical instruments and methods, preparation of azo dyes, animal/human proteins, etc.
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Embodiment 1
[0023] Add 2.0g (4.4mmol) of sunset yellow and 25ml of anhydrous toluene into a 100ml round bottom flask, slowly add 2.0ml (28.1mmol) of thionyl chloride under electromagnetic stirring, then drop a few drops of anhydrous DMF, and stop after reflux for 2h reaction. Remove the remaining thionyl chloride and toluene by rotary evaporation, add petroleum ether, filter with suction, and dry to obtain compound I as a dark red solid.
Embodiment 2
[0025] Add 0.17g (1.35mmol) glycine methyl ester hydrochloride, 20ml anhydrous acetone, 0.27g triethylamine to a 50ml round bottom flask, stir to dissolve, add 0.2g (0.45mmol) sunset yellow sulfonyl chloride I, and stir at room temperature for 1h. Acetone was distilled off and separated by silica gel column chromatography to obtain product IIA (R=H).
[0026] 1 H NMR (CDCl 3 , 400M) δ8.67 (d, 1H, J=8.8Hz, Ar-H 5 ), 8.24(s, 1H, Ar-H 3 ), 8.14 (d, 1H, J=9.6Hz, Ar-H 2 ), 8.05(d, 2H, J=8.4Hz, Ar-H 6,6’ ), 7.95(s, 1H, Ar-H 4 ), 7.91 (d, 2H, J=8.4Hz, Ar-H 7,7’ ), 6.96 (d, 1H, J=9.6Hz, Ar-H 1 ), 3.77 (d, 4H, J=7.2Hz, CH 2 ×2), 3.54(s, 3H, -OCH 3 ), 3.51(s, 3H, -OCH 3 ),.
[0027] HRMS (ESR): m / z=573.0726 (caled.for573.0720[M+Na] + )
Embodiment 3
[0029] Add 0.29g (1.35mmol) L-phenylalanine methyl ester hydrochloride, 20ml anhydrous acetone, 0.27g triethylamine into a 50ml single-necked round bottom flask, stir until dissolved, add 0.2g (0.45mmol) sunset yellow Acid chloride I, stirred at room temperature for 1h. Acetone was distilled off and separated by column chromatography to obtain the product IIA (R=CH 2 Ph).
[0030] 1 H NMR (CDCl 3 , 400M) δ16.13 (s, 1H, OH), 8.41 (d, 1H, J=8.4Hz, Ar-H 5 ), 7.91(s, 1H, Ar-H 3 ), 7.78 (d, 3H, J=8.4Hz, Ar-H 6,6’,2 ), 7.63 (d, 3H, J=8.4Hz, Ar-H 7,7’,4 ), 7.18(d, 3H, J=6.8Hz, Ar-H), 7.13(d, 3H, J=7.2Hz, Ar-H), 7.05(d, 1H, J=7.2Hz, Ar-H), 6.90(d, 1H, J=8.4Hz, Ar-H 1 ), 5.82-5.88(m, 2H, 2×NH), 4.23-4.26(m, 2H, 2×CH), 3.51(s, 3H, -OCH 3 ), 3.46(s, 3H, -OCH 3 ), 2.96-3.08 (m, 2H, 2×CH 2 ).
[0031] HRMS (ESR): m / z = 753.1654 (caled. for 753.1659 [M+Na] + )
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