Preparation of 3-(PolystyrylsuIfonyl) propanol and It's Application in Solid-Phase Organic Synthesis

Abstract

Abstract:

Synthesis of 3-(polystyrylsulfonyl)propanol resin and its application in solid-phase organic synthesis is reported. Polystyrene sodium sulfinate 1 reacted with 3-chloropropanol in the presence of the phase transfer catalyst Bu₄NI and cocatalyst KI to give the 3-(polystyrylsulfonyl)propanol resin 2. The use of resin 2 as a solid support in solid-phase synthesis was discussed. Boc-L-Ala was immobilized onto resin 2 to give resin 3. Hie remaining hydroxyl group was blocked by benzoyl chloride. Then the Boc-protecting group was removed with 6 mol/L HCl in dioxane and then neutralized with Et₃N to afford resin 5. Resin 5 was reacted with phenyl isocyanate to give polymer-supported urea 6. Resin 6 was treated with 6 mol/L hydrochloric acid or a saturated mixture of sodium methoxide in methanol to give N-phenyl-4-methyl hydantoin, while resin 6 was cleaved with a solution of dioxane/methanol/4 mol/L sodium hydroxide (V:V:V=30:9:l)(containing 0.1 mol/L NaOH) to afford N-(α-methyl) carboxymethyl-N'-phenyl urea.

Key words: Solid-phase organic synthesis, 3-(Polystyrylsulfonyl)propanol, Hydantoin, Urea

CLC Number:

O621.3

TrendMD:

SUN Wei-Min, HUANG Wen-Qiang. Preparation of 3-(PolystyrylsuIfonyl) propanol and It's Application in Solid-Phase Organic Synthesis[J]. Chem. J. Chinese Universities, 2001, 22(S1): 218.

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Preparation of 3-(PolystyrylsuIfonyl) propanol and It's Application in Solid-Phase Organic Synthesis

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