Polymer precursors of radiolabeled compounds, and methods of making and using the same
a radiolabeled compound and polymer precursor technology, applied in the direction of peptides, isotope introduction of acyclic/carbocyclic compounds, organic compounds of the group 3/13 element, etc., can solve the problems of short shelf life, chemical purity and isotopic purity, and the presence of toxic tin by-products,
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example 1
(4S,5S)-2-(3-bromophenyl)-3,4-dimethyl-5-phenyl-1,3-oxazolidine (7)
[0230] Into a one necked 250 mL round-bottom flask, equipped with a Dean-Stark trap and a condenser was placed 8.78 g (47.5 mmol) of 3-bromobenzaldehyde and 7.83 g (47.4 mmol), of (S,S)-(+)-pseudoephedrine followed by 180 mL of benzene. After reflux for 18 hrs, the benzene was removed using a rotary-evaporator, to give a yellow oil, which solidified upon standing. A white solid (mp. 73-75° C.) was obtained after recrystallization from hexanes, 14.78 g (94%).
[0231]1H NMR (CDCl3) ppm: 7.75 (s, 1H), 7.51-7.26 (m, 8H), 4.93 (s, 1H), 4.76 (d, 1H), 2.56 (m, 1H), 2.23 (s, 3H), 1.23 (d, 3H). 13C NMR ppm: 141.96, 139.91, 132.08, 130.95, 129.86, 128.37, 128.00, 126.76, 126.61, 122.50, 98.60, 86.60, 68.62, 35.12, 14.23.
example 2
(4S,5S)-2-(4-bromophenyl)-3,4-dimethyl-5-phenyl-1,3-oxazolidine (8)
[0232] In an analogous manner, 500 mg (2.7 mmol) of 4-bromobenzaldehyde, 450 mg (2.7 mmol), of (S,S)-(+)-pseudoephedrine and 40 mL of benzene were refluxed for 18 hrs. Solvent evaporation yielded a viscous yellow oil, 883 mg (98%).
[0233]1H NMR (CDCl 3): 7.42 (d, 2H), 7.35-7.20 (m, 7H), 4.82 (s, 1H), 4.65 (d, 1H), 2.45 (m, 1H), 2.09 (s, 3H), 1.12 (d, 3H). 13C NMR: 139.97, 138.53, 131.38, 129.68, 128.33, 127.94, 126.56, 122.91, 98.69, 86.50, 68.59, 35.00, 14.19.
example 3
Poly-(4S,5S)-2-(3-{dibutyl[2-(3-and 4-vinylphenyl)ethyl]stannyl}phenyl)-3,4-dimethyl-5-phenyl-1,3-oxazolidine)-co-divinylbenzene (9)
[0234] The protected 3-bromobenzaldehyde 7, (2.90 g, 8.7 mmol), was added into a three-necked 200 mL round-bottom flask, equipped with a T-bore stopcock, a rubber septum and a powder addition side arm containing 4.01 g of chlorostannane polymer 10 (˜5.9 mmol of SnCl). Under a flow of argon, 80 mL of freshly distilled dry THF was added by syringe. The flask and its contents were outgased three times at dry ice / acetone temperatures and an argon atmosphere was introduced. To the solution of 7 in THF at −78° C., n-butyllithium (3.0 mL, 7.5 mmol, 2.5 M) was added dropwise with the resultant formation of a yellow color. After 2 h at −78° C., the polymer was tipped into the THF solution, and the suspension was allowed to stir for 18 h and warm slowly to RT. To the suspension about 3 mL of methanol was added and the suspension was filtered. The solid was washe...
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