Phoxime resin

Scialdone MA, Shuey SW, Soper P, Hamuro Y, Bums DM. Phosgenated p-nitrophenyl(polystyrene)ketoxime or phoxime resin. A new resin for the solid-phase synthesis of ureas via thermolytic cleavage of oxime-carbamates. J Org Chem 1998 63 4802-4807. 

Figure 6.22 SP automated chemistry assessment for the urea library L6 from Phoxime resin 6.53.

Thiohydantoins have been similarly prepared following the first route but using isothiocyanates [98]. Sulfahydantoins have been also prepared using sulfamoyl chloride [99]. The phoxime resin (phosgenated oxime resin, 19, see Section 15.2.1.1.1) has been used to synthesize 3-aminohydantoins from the oxime carbamates [100]. 

Recently, Scialdone and colleagues have employed phosgenated />-nitrophenyl(poly-styrene) ketoxime (Phoxime, 76) resin in the synthesis (via 77 and 78) of acyclic and heterocyclic amino-acid-derived ureas 79 too (Scheme 42). Resin 75 was first reacted with an amino acid and TMSCl in pyridine, and the resulting carbamate acid resin 77 was then coupled with an amine under standard carbodiimide protocol (HOBt/DIC in DMF) to obtain the carbamate amide resin 79. 

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