high-throughput puri cation: triage and optimization in .NET framework

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high-throughput puri cation: triage and optimization
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MW-triggered HPLC puri cation is selected as the method of choice when large libraries are submitted with high variability in reaction yield. When no good UV chromophore is present in the reaction products, either ELSD-triggered fraction collection as described above or MW-triggered fraction collection must be employed. The requisite for fraction collection triggered by MW is the presence of a good ionizable group within the reaction product. Approximately one-half the face time is necessary on the part of HTP staff technicians for MW-triggered puri cation due to the elimination of a second MS validation step and sample sorting after UV-triggered puri cation. Therefore the single MW-triggered HPLC available to HTP is used at capacity at all times. SFC is selected as the puri cation method of choice for several sample types. As SFC is a normal-phase chromatography technique, it is used for the puri cation of highly lipophilic compounds. When the submitting chemist requests that TFA not be used in puri cation, SFC may be used as an alternative to the less desirable ammonium acetate buffer alternative in HPLC. SFC can offer advantages in terms of increased resolution, hence crude samples with a high degree of complexity are preferentially puri ed by SFC. The requisite for puri cation by SFC is good solubility of material in an injection solvent compatible with carbon dioxide (typically methanol, dichloromethane, acetonitrile, and mixtures thereof) and, since this system is set up only in a UV-triggered mode, a good UV chromophore. In general, we have worked out methods speci c for the puri cation of the standardized chemistries generated by the HTOS group,21 so SFC is applied only to the puri cation of libraries from this client set. Since HTOS represents approximately one-half of the total number of samples submitted to HTP, this instrument is always used at capacity.
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LIBRARY PURIFICATION EXAMPLES
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The following examples (selected from typical structural types synthesized for the purpose of puri cation triage) illustrate application of each of the puri cation systems described above: UV-triggered HPLC, MW-triggered HPLC, and UV-triggered SFC. Upon submission of libraries to HTP, each of the three puri cation technologies is considered in terms of the relative merits and liabilities of the technique. The library characteristics evaluated include sample weights, sample set sizes, variability of yields within a library, the presence of good UV chromopore or good MS ionization character, and nally what samples are in process and those in queue as this affects instrumentation readily available at the time of submission. Each of the exam-
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library puri cation examples
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ples in the following sections depicts the puri cation of a single member from a set of similar samples submitted as a set. 11.3.1. UV-Triggered HPLC Puri cation Examples
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UV-triggered HPLC represents the highest capacity instrumentation currently available within HTP. Therefore it is employed for the puri cation of most routine samples when a good UV chromophore is present. The ELSD-triggered format available on this same instrumentation is initiated only if necessary, as it is somewhat less reliable than is UV-triggered fraction collection. Owing to the large numbers of such sets submitted on a daily basis, all small sample sets (of one through six members) are puri ed by UV-HPLC if feasible. Example 1 was a set of two reductive amination reaction samples submitted for puri cation. Each sample was approximately 200 mg and therefore was above the weight that can be processed in a single injection by our SFC instrumentation. As it is both more ef cient and more desirable for the synthetic chemist that materials be puri ed and returned as a single fraction, HPLC was the method of choice for puri cation in this case. Each of the two samples had a good UV chromophore at both 220 and 254 nm and was therefore amenable to UV-triggered fraction collection. As a routine, high-weight, small sample set with good UV characteristics, UVtriggered HPLC was the method selected for processing. Figure 11.4A and 11.4B depict the structure and chromatography for one member of this sample set. Example 2 was a 48-membered library of amine formation reaction products submitted for puri cation. Each sample was approximately 50 mg in weight, and all reactions proceeded with similar high yields. Each sample had a good UV chromophore at 220 nm, which was distinct from other reaction components as evidenced by the analytical HPLC/MS supplied upon submission. Therefore as routine library with a good UV product chromophore and similar reaction yields, HPLC, UV triggered at 220 nm was selected as the puri cation method for this library. Figure 11.5A and 11.5B depict the structure and chromatography, respectively, for a representative member of this library. 11.3.2. MW-Triggered HPLC Examples
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A single MW-triggered HPLC instrument represents the total capabilities of this technology within HTP and is generally employed at capacity. Therefore this technique must often selected only when necessary, such as for the
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