HO2C OH Wang resin in .NET framework

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HO2C OH Wang resin
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NHFmoc
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DIC, DMAP, DMF O
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O NHFmoc
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Scheme 3.2. FMOC coupling to Wang resin.
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for the presence of hydroxy groups (Figure 3.4, non uorescent beads) and the single-bead FTIR results (Figure 3.3) indicated a complete coupling of the protected amino acids to the Wang resin.
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PRECURSOR VALIDATION USING FTIR
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Rigorous validation of all building blocks is required for a highly diverse combinatorial library to have good yield and purity. In the course of vali-
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1710 cm-1
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Absorbance
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Fmoc Coupled Resin 3437 cm-1
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Wang Resin
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3500 3000 2500 2000 1500 1000
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Wavenumbers (cm-1)
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Figure 3.3 Single-bead FTIR spectra of Wang resin 4 (bottom) and resin 6 (top). Disappearance of the hydroxy group (broad stretch at 3437 cm-1) and the appearance of the carbonyl group (strong stretch at 1710 cm-1) indicate the coupling of the FMOC carboxylic acid 5 to the Wang resin.
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Figure 3.4 Resin-bound alcohol uorescent test. Non uorescent beads on left indicate the absence of hydroxyl group, and uorescent beads on right indicate presence of hydroxyl group.
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R1NH2 OMe O H O OMe AcOH, NaBH(OAc)3, THF O OMe NR1H OMe
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Step A
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Cl DIPEA, DMF Cl N R2 Cl N
Step B
Cl R1HN N R2 N 25%TFA/DCM O
OMe N R1 OMe N
N R2
Scheme 3.3. Library 1 scheme with cleavage step.
dation studies this can be accomplished by the combination of color test and FTIR analysis without an extra cleavage step needed for LC/MS analysis. The rst test case was to validate the amine precursors for an aryl pyrimidine library (Lib 1) on solid phase (Scheme 3.3).10 Reductive amination was carried out on 4-formyl-3,5-dimethoxyphenoxymethyl resin 7 (step A), followed by the addition of an amines 8 to the resin (step B) to form 9. An aldehyde functional group on the bead was transformed to a secondary amine in step A, which would result in the disappearance of IR bands for C = O stretch from aldehyde at 1683 cm-1 and C H stretch at 2775 cm-1 (Figure 3.5). Step A progressed in two stages. The intermediate is an imine 11 that is further reduced to the secondary amine 9 (route 1 of Scheme 3.4). Route 2 of Scheme 3.4 illustrates that an alcohol 12 would be formed after reduction treatment if the conversion of 7 to 11 were not complete. To examine if route 2 occurred, a uorescent test for resin bound hydroxyl8 was used in addition to single-bead FTIR analysis. The uorescence dye 9anthroylnitrile speci cally reacts with the hydroxyl group, and not the secondary amines.8 After the reductive amination with an amine, the disappearance of the IR stretches associated with the aldehyde group and the negative result for the presence of hydroxyl group indicated that the reaction went to completion.
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2775 cm-1
1683 cm-1
Absorbance
4-Formyl-3,5-dimethoxyphenoxymethyl reduced resin
4-Formyl-3,5-dimethoxyphenoxymethyl resin
Wavenumbers (cm-1)
Figure 3.5. Single-bead FTIR spectra of 4-formyl-3,5-dimethoxyphenoxymethyl resin 7 (bottom) and reduced resin 9 (top). Disappearance of the aldehyde groups (strong stretch at 1679 cm-1 and weak stretch at 2775 cm-1) and the lack of formation of hydroxyl signal indicate the successful reductive amination of resin 7.
A total of 59 amines (Chart 3.1) were examined by both uorescence test and single-bead FTIR.A selection of FTIR spectra of resin 9 was shown in Figure 3.6. The IR spectrum of 4-formyl-3,5-dimethoxyphenoxymethyl resin showed an IR band for aldehyde C = O stretch at 1683 cm-1 (Figure 3.6A). The rest of the spectra in Figure 3.6 (from B to H) showed decreased intensity in this band. For quantitative analysis, an integration analysis of this band was carried out. All integration values were normalized to a polystyrene band at 1947 cm-1. Assuming the integrated IR band for C = O stretch from 4-formyl-3,5-dimethoxyphenoxymethyl resin was 100%, the relative percentage completion of each amine was calculated from their integrated bands at 1683 cm-1. A summary of FTIR results for all 59 amines was listed in Table 3.1. Among the 59 amines evaluated, only amine 33 did not give desired product at all, while amines 34 and 44 showed less than 50% completion, the rest of them showed greater than 95% completion. The broad feature from O H stretch of alcohol in the range of 3200 to