Synthesis of polyether-bound 3-(5-fluorouracil-1-yl)propanoic acid and its hydrolysis reactivity

Matrix polarity effects on microphase separation in zwitterionomers, 1. Synthesis of the model random zwitterionomers

“…in 8C 1.46 6 10 4 versus DP w (PEC) l 1.62 6 10 4 as opposed to the degradation observed by Ouchi et al [25] , DP n l 2.43 6 10 3 versus DP n (PEC) l 3.61 610 3 , despite identical experimental conditions. The basic hydrolysis step carried out in the original experimental conditions as described for run 1 in Tab.…”

“…1, the original process corresponding to run 4 may be improved with respect to the overall yield (only 50% according to Cohen, [24] see polymer recovery in the Experimental part) and to the molecular weight: chain degradation cannot be avoided but limited by a small decrease of the reaction temperature without too much loss at the level of the PGOH purity. b) Ouchi's method [25] dissociates the preparation of PGAC (S N 2 substitution assisted by a phase transfer catalyst) from its basic hydrolysis, as shown in Scheme 3. In our hands, the first step (see Experimental part) leads to PGAC without significant chain scission DP w l Scheme 2: Synthesis of PGOH from PEC according to Cohen [24] (one step) and Ouchi [25] (two steps) methods Tab.…”

“…b) Ouchi's method [25] dissociates the preparation of PGAC (S N 2 substitution assisted by a phase transfer catalyst) from its basic hydrolysis, as shown in Scheme 3. In our hands, the first step (see Experimental part) leads to PGAC without significant chain scission DP w l Scheme 2: Synthesis of PGOH from PEC according to Cohen [24] (one step) and Ouchi [25] (two steps) methods Tab. 1.…”

“…c) From light scattering experiments in acetone solution. d) Ouchi's experimental conditions[25] .e) In situ hydrolysis of the PGAC derived from PEC: ternary solvent DMF : CH 3 OH : H 2 O 3 1 : 0.5 : 0.25 by vol. ; [PGAC] L 3.2 g N dL -1 (L 0.31 mol N L -1 ).…”

Polymers in the Pharmaceutical Applications - Natural and Bioactive Initiators and Catalysts in the Synthesis of Biodegradable and Bioresorbable Polyesters and Polycarbonates

“…For example, 5-fluorouracil can be applied locally or orally in the therapy of the alimentary tract, urinary bladder and prostate gland cancers. The conjugations of this therapeutic agent as a pendant group to polyethylene glycol (Ouchi et al, 1986(Ouchi et al, , 1992 or to vinyl polymer chain as substituent form examples of its macromolecular prodrugs (Ouchi et al, 1988).…”