Amino-polystyrene resin

Aube and co-workers have found that enolizable ketones react with benzyl azide in triflic acid to yield /V-(phenylamino)-methylated products [Eq. (5.354)]. The transformation is an aza-Mannich reaction interpreted with the involvement of the Mannich reagent A -phenyl iminium ion 295 formed in situ in a Schmidt rearrangement. Cyclic tertiary alcohols react with alkyl azides in triflic acid to yield N-alkylamines (296, 297)983 [Eq. (5.355)]. The Schmidt rearrangement was used to transform Merrifield resin into amino-polystyrene resin by reacting the azido derivative in excess triflic acid (CH2CI2, 0°C).984... 

Moore, S., Spackman, D., and Stein, W. H., 1958. Chromatography of amino acids on sulfonated polystyrene resins. Analytical Chemistry 30 1185-1190. 

Amine bound to a Wang-polystyrene resin 381 was acylated with 4-oxo-4Ff-pyrido[l,2-u]pyrazine-3-carboxylic acid in the presence of bromotrispyrrolidinophosphonium hexafluorophosphate and /-Pr2NEt in A-methylpyrrolidone (98MIP16). l-(4-Cyclohexyl-4-r / r-butylaminocarbo-nyl-l-piperidyl)-2-(4-fluorophenyl)ethylamine was acylated with perhydro-pyrido[l,2-u]pyrazine-3-carboxylic acid (01MIP19). An amino group of a macrocyclic compound attached to a solid support was acylated with... 

Amino acids are separated in their native form on a sulphonated polystyrene resin using a system of sodium or lithium based buffers. Separation is effected by stepwise, rather than gradient elution, and the chromatography can be further optimized by carefully controlling the temperature of the analytical column. 

The separation takes place in a column of sulphonated cross-linked polystyrene resin, which is a strong cation exchanger. The matrix of the resin is strongly anionic in nature (S03 ) and at the low pH used initially, the amino acids will be positively charged and will be attracted to the negatively charged sulphonate groups. 

Attachment of Compound 11 onto an Aminomethylated Polystyrene Resin 1 3141 A 1% cross-linked aminomethylated polystyrene resin (0.83 mmol of amino group per gram of resin, 2.41 g, 2 mmol) was placed in an ATC Model 90 reaction vessel (capacity 200 mL) and the resin washed successively with NMP, 10% DIPEA in NMP, and NMP. Then, 11 (1.41 g, 3 mmol, 1.5 equiv), HBTU (1.14 g, 3 mmol), and HOBt (0.41 g, 3 mmol) were dissolved in NMP (20 mL) in a flask, and DIPEA (0.78 mL, 4.5 mmol) was added to the soln immediately. The mixture was introduced into the reaction vessel containing the resin within 2 min after addition of DIPEA, and the entire mixture was agitated for lh at rt. The soln was drained from the reaction vessel and the resin washed well with NMP. The completion of the coupling reaction was confirmed by a ninhydrin test. 

Scheme 8 shows how this synthesis was performed. FMOCprotected methoxy-3-amino-benzoic acid 62 was attached to hydroxymethyl polystyrene resin. The resulting ester 63 was deprotected and then reductively... 

Figure 3-6 Separation of amino acids by cation-exchange chromatography on a sulfonated polystyrene resin in the Na+ form by the method of Moore and Stein.110 The amino acids were detected by reaction with ninhydrin (Box 3-C) areas under the peaks are proportional to the amounts. Two buffers of successively higher pH are used to elute the amino acids from one column, while a still higher pH buffer is used to separate basic amino acids on a shorter column. From Robyt and White.13...

A library of di- and trisubstituted 5-amino-l 77-1-benzazepine derivatives was assembled through attachment of a preformed 1-benzazepine unit to an aminomethylated polystyrene resin. The initial solution phase synthesis of the 1-benzazepine moiety was based on an intramolecular Dieckmann cyclization (type d) followed by a ketone to primary amino group transformation via reduction ( NaBH3CN) of an imine intermediate <2007JC0487>. 

Cross-linked polystyrene resins incorporating chiral amino acids were utilized as the chiral stationary phases (CSPs) in CLEC [6,21], Davankov et al. [12] reported the use of a resin incorporating L-proline in a polystyrene-type matrix. The resin was prepared by reacting L-proline with the chlormethylated styrene-divinyl-... 

M. A. Pericas, A. Riera, and J. K. Sanders, High catalytic activity of chiral amino alcohol ligands anchored to polystyrene resins,/. Org. Chem. 1998, 63, 6309-6318. 

In order to investigate dendrimers of a different nature [230], Bradley described the synthesis and transfection efficiency of polyamidourea dendrimers synthesised from isocyanate-containing AB3 monomers [231-234]. The use of this kind of tris-branched building block was addressed to enhance dendrimer synthesis by replacement of the 1,4-addition step typical of PAMAM synthesis and to a rapid increase in terminal functionality. The dendritic structures were synthesised using a divergent, microwave-assisted, solid-phase approach with the dendrimers assembled on polystyrene resin via an acid labile linker (see Fig. 26). In particular, a G3.0 polyamidourea bis-dendron with the peripheral amino groups conjugated to L-lysine residues demonstrated remarkable transfection abilities [234],... 

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