Synthesis of 2-Polystyrylsulfonylethanol and Its Application in Solid-phase Organic Synthesis of Hydantoins and Ureas

Abstract

Abstract: In this article a new kind of polymer-support: 2-polystyrylsulfonylethanol was prepared and used in solid-phase organic synthesis. Sodium polystyrylsulfinate resin 1 reacted with chloroethanol in the presence of phase transfer catalyst Bu4NIand KIas a cocatalyst to give 2-polystyrylsulfonylethanol resin 2 After the esterification of resin 2 with Boc-Gly, deprotection of Boc group with HCl, neutralization by Et₃N, conversion of the free amino group with phenyl isocyanate or phenyl isothiocanate to urea to give urea resin 6 The urea resins 6a and 6b were cleaved with 6 mol/L HCl to obtain the hydantoin derivatives 7a and 7b in an overall yields of 29%—30%. While the resin 6 was treated with 4 mol/L NaOHthen HCl to give the urea derivatives 8a and 8b in an overall yields of 20%—21%. The whole synthesis processes were optimized by the trace of the reactions by using IRspectra. The results show that resin 2 can easily form a stable ester linker with carboxylic acids and this kind of linker can be cleaved by the use of both strong acid or dilute base.

Key words: 2-Polystyrylsulfonylethanol, Solid-phase synthesis, Hydantoin, Thiohydantoin, Urea, Thiourea

CLC Number:

O621.3

TrendMD:

CHENG Shao-Ling, HUANG Wen-Qiang. Synthesis of 2-Polystyrylsulfonylethanol and Its Application in Solid-phase Organic Synthesis of Hydantoins and Ureas[J]. Chem. J. Chinese Universities, 2002, 23(9): 1809.

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Synthesis of 2-Polystyrylsulfonylethanol and Its Application in Solid-phase Organic Synthesis of Hydantoins and Ureas

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