Solid-Supported Reagents. Save Time and Achieve Higher Purities
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1 Solid-Supported Reagents Save Time and Achieve Higher Purities
2 Solid-Supported Reagents and Scavengers Accelerate a wide range of solution-phase reactions and work-ups with Biotage's scavenger resins and solid-supported reagents. Solid-supported reagents allow chemists to rapidly separate mixture components by simple filtering or decanting, often eliminating the need for liquid-liquid extraction, chromatography, or crystallization. In addition, Biotage's supported reagents provide unique benefits, such as selectivity and immobilization of toxic intermediates. Solid-Supported Reagents Solid-supported reagents, also known as polymer-bound or resin-bound reagents, are functionalized polymers that perform synthetic transformations in the same manner as their non-bound counterparts. They can be used as reactants in solution-phase or as supports for solid-phase organic synthesis (SPOS). In solution-phase chemistry, spent reagents are simply filtered off leaving the desired product in solution. In SPOS, on the other hand, the product is isolated by filtration leaving spent reagents in solution. In either case, product isolation is expedited through simply filtering or decanting, in some cases negating the need to further purify the product. Figure 1. Solid-supported reagents simplify product purification, because spent and excess reagents can be removed by filtration. Biotage offers a wide range of supported reagents including reducing agents, oxidants, acids, bases and even catalysts anchored to solid supports. Scavengers Unlike solution-phase chemistry, polymer-bound reagents and scavengers can be added together into reactions. Multiple resins can be used together in a single pot as even incompatible functional groups will not interact when bound to a solid support. Figure 2. Example of polymer-assisted organic synthesis. The solidsupported triphenylphosphine is converted to the triphenylphosphine oxide during transformation of the azide to the amine in the Staudinger reaction. Figure 3. Classic synthesis and purification of N-substituted pyrazolines using multiple scavenger resins. Following synthesis a purification cocktail containing multiple scavenger resins was used to remove unreacted pyrazoline and electrophile. Reaction conditions: (1) R 3 COCl, PS-DIEA, (2) R 3 NCO, (3) R 3 SO 2 Cl, PS-DIEA, (4) R 3 OCOCl, PS-DIEA Purification cocktail: and PS-Isocyanate Bauer, U. et al. Tetrahedron Lett. 2000, 41, Solid-Supported Reagents Biotage 2014
3 Solvent Compatibility/Microwave Chemistry Solvent Compatibility Lightly cross-linked polystyrene resins require the use of solvents that swell the resin to allow reagents to gain access to the resin-bound functional groups. If the reaction solvent does not swell the resin, it may be necessary to add a co-solvent that is compatible with the resin. In this brochure, lightly crosslinked polystyrene resins have a PS- prefix. More highly cross-linked macroporous resins have a permanent pore network and do not require the use of a swelling solvent. These resins are effective in any solvent that is not reactive with the resin open functionality. In addition, macroporous resins do not swell or undergo a significant volume change in contrast to their polystyrene counterparts. In this brochure, the names of macroporous resins have a MP- prefix. Microwave Chemistry and Solid- Supported Reagents Combining microwave-assisted organic synthesis (MAOS) with solid-supported reagents and scavengers can further impact the discovery process by decreasing reaction times while still taking advantage of an expedited work-up. A variety of transformations can be accelerated using microwave energy including substitutions, additions and organometallic reactions. In addition to speeding up reactions, microwave heating may also enable the use of solvents that are traditionally considered non-swelling solvents in relation to low crosslinked PS-resins. Figure 4. Synthesis of a 1,5-diarylpyrazole. Reference: Humphries, P.S. and Finefield, J.M. Tetrahedron Lett. 2006, 47, , Biotage Technical Note TN Synthesized Product Base Solvent or Acid Time (Conventional Heating) Yield (Conventional Heating) Time (Microwave Heating) Enol ketone 3 NaH, DME 2 h 60% 10 min 95% Pyrazole 5 ptsoh 7 h 95% 5 min 61% Pyrazole 5 Si-TsOH 6 h 84% 5 min 95% Yield (Microwave Heating) Table 4. Effect of microwave heating on reaction time and yield. Microwave heating was performed at 160 C and conventional, non-microwave heating was performed at 100 C. 3
4 Scavengers for Electrophiles/Nucleophiles Scavengers for Electrophiles Scavengers for Nucleophiles Which Compounds to Scavenge? Recommended Scavengers Carbonyls PS-TsNHNH 2 Alkylating agents: Alkyl halides, Mesylates, Tosylates, α-bromoesters, α-bromoketones Acid chlorides Sulfonyl chlorides Isocyanates Epoxides Oxophilic inorganic, organometallic complexes Lewis acids, e.g., Ti(IV), Sn(IV) Pd(II), Pd(O), Pt, Cu Table 2. Scavengers for electrophiles. PS-Thiophenol PS-Triphenylphosphine Si-Thiol PS-NH 2 PS-NH 2 PS-TsNHNH 2 PS-Triamine PS-NH 2 PS-Thiophenol Si-Thiol PS-DEAM MP-TMT PS-TBD Si-Thiol Which Compounds to Scavenge? Alcohols Amines: primary/secondary Amines: Selective for primary Amines: Anilines (Aromatic) Hydrazines Enolates Thiols/Thiolates Alkoxides Reducing agents Acids/Acidic phenols: HOBt Pentafluorophenol 4-Nitrophenol Carboxylic acid Phenol Boronic acid Table 3. Scavengers for nucleophiles. Recommended Scavengers PS-TsCl(HL) PS-Isocyanate MP-Isocyanate PS-TsCl(HL) Si-TsOH (SCX-3) Si-Propylsulfonic Acid (SCX-2) PS-Benzaldehyde PS-TsCl(HL) PS-Isocyanate MP-Isocyanate Si-Propylsulfonic Acid (SCX-2) PS-Benzaldehyde PS-TsCl(NH) PS-Benzaldehyde PS-Isocyanate MP-Isocyanate PS-Thiophenol Si-Thiol PS-TsCl(HL) PS-Isocyanate MP-Isocyanate PS-Benzaldehyde MP-Carbonate PS-TsNHNH 2 Si-Carbonate Figure 5. is an example of an electrophilic scavenger that can be used to remove electrophiles such as acid chlorides and isocyanates. Figure 6. PS-Isocyanate is an example of a nucleophilic scavenger that can be used to remove nucleophiles such as amines and alkoxides. 4 Solid-Supported Reagents Biotage 2014
5 Solid-Supported Reagents Solid-Supported Reagents What Type of Reagent? What Application? Acids and Bases Basic Quenching, Neutralize Ammonium Salts Acid Quenching Strong Tertiary Amine Base (e.g. mesylate formation) Tertiary Amine Base (e.g. formation of amides, sulonamides, carbamates) Strong Base (e.g. alkylation of phenols, amines, activated methylene compounds, esterification of carboxylic acids) Amine purification Coupling Agents Amide synthesis Activated ester formation Recommended Solid- Supported Reagent MP-Carbonate Si-Carbonate PS-DIEA PS-DIEA PS-NMM PS-TBD Si-Propylsulfonic acid (SCX-2) PS-Carbodiimide PS-HOBt(HL) PS-HOBt(HL)/ACTU PS-DIEA PS-HOBt(HL)/ACTU What Type of Reagent? What Application? Recommended Solid- Supported Reagent Reducing Agents Carbonyl Reduction MP-BH 4 Reductive Amination MP-CNBH 4 MP-BH(OAc) 3 MP-BH 4 (with Ti(O i Pr) 4 ) Oxidizing Agents Alcohols to Aldehydes Electrophilic Activation Halogenation (Chlorination, bromination, iodination) Phenylether Formation (i.e. Mitsunobu reaction) Thioester Active Intermediate Alcohol Activation (tosylation) Acid and Sulfonyl Chloride Activation Nucleophilic Activation Carbon-Carbon Bond (e.g. Wittig reaction) Sulfonyl Hydrazone Formation (e.g. Hurd-Mori thiadiazole synthesis) PS-TEMPO PS-Triphenylphosphine PS-Triphenylphosphine PS-Thiophenol PS-TsCl PS-Triphenylphosphine PS-TSNHNH 2 Si-Tosyl-Hydrazine Protecting Group Cleavage BOC cleavage BSMOC, FMOC Table 4. Solid-supported reagents. Si-Propylsulfonic acid (SCX-2) Catalysts Acids Acyl Transfer C-C Coupling Si-Propylsulfonic acid (SCX-2) PS-PPh3-Pd Figure 7. Examples of synthetic transformations using solid-bound triphenylphosphine. Figure 8. Strong cation exchange resin, Si-supported propylsulfonic acid. 5
6 Ordering Information Ordering Information Part Number Description Size PS-HOBt (HL) 3 g PS-HOBt (HL) 10 g PS-HOBt (HL) 25 g PS-HOBt (HL) 100 g PS-HOBt (HL) 1,000 g PS-NMM 3 g PS-NMM 10 g PS-NMM 25 g PS-NMM 100 g PS-NMM 1,000 g PS-PPh 3 -Pd 1 g PS-PPh 3 -Pd 10 g PS-PPh 3 -Pd 25 g PS-PPh 3 -Pd 100 g PS-TBD 3 g PS-TBD 10 g PS-TBD 25 g PS-TBD 100 g PS-TBD 1,000 g MP-Triacetoxyborohydride 3 g MP-Triacetoxyborohydride 10 g MP-Triacetoxyborohydride 25 g MP-Triacetoxyborohydride 100 g MP-Triacetoxyborohydride 1,000 g PS-Triphenylphosphine 3 g PS-Triphenylphosphine 10 g PS-Triphenylphosphine 25 g PS-Triphenylphosphine 100 g PS-Triphenylphosphine 1,000 g ACTU 3 g ACTU 10 g ACTU 25 g ACTU 100 g ACTU 1,000 g MP-Borohydride 3 g MP-Borohydride 10 g MP-Borohydride 25 g MP-Borohydride 100 g MP-Borohydride 1,000 g PS-Carbodiimide 3 g PS-Carbodiimide 10 g PS-Carbodiimide 25 g PS-Carbodiimide 100 g PS-Carbodiimide 1,000 g MP-Carbonate 3 g MP-Carbonate 10 g MP-Carbonate 25 g MP-Carbonate 100 g MP-Carbonate 1,000 g PS-NH 2 3 g PS-NH 2 10 g PS-NH 2 25 g PS-NH g PS-NH 2 1,000 g Part Number Description Size MP-Cyanoborohydride 3 g MP-Cyanoborohydride 10 g MP-Cyanoborohydride 25 g MP-Cyanoborohydride 100 g MP-Cyanoborohydride 1,000 g PS-DIEA 3 g PS-DIEA 10 g PS-DIEA 25 g PS-DIEA 100 g PS-DIEA 1,000 g g g g g ,000 g g g g ,000 g PS-Isocyanate 3 g PS-Isocyanate 10 g PS-Isocyanate 25 g PS-Isocyanate 100 g PS-Isocyanate 1,000 g PS-Ts-NHNH 2 10 g PS-Ts-NHNH 2 25 g PS-Ts-NHNH g PS-Ts-NHNH 2 1,000 g PS-Thiophenol 10 g PS-Thiophenol 25 g PS-Benzaldehyde 10 g PS-Benzaldehyde 25 g PS-Benzaldehyde 100 g PS-Benzaldehyde 1,000 g PS-TsCL(HL) 10 g PS-TsCL(HL) 25 g PS-TsCL(HL) 100 g PS-TsCL(HL) 1,000 g PS-DEAM 10 g PS-DEAM 25 g PS-DEAM 100 g MP-TsOH 10 g MP-TsOH 25 g MP-TsOH 100 g MP-TsOH 1,000 g g g g ,000 g ISOLUTE (EC) 10 g ISOLUTE (EC) 25 g ISOLUTE (EC) 100 g ISOLUTE (EC) 500 g ISOLUTE (EC) 1,000 g 6 Solid-Supported Reagents Biotage 2014
7 Ordering Information Part Number Description Size g g g g ,000 g ISOLUTE (EC) 10 g ISOLUTE (EC) 25 g ISOLUTE (EC) 100 g ISOLUTE (EC) 500 g ISOLUTE (EC) 1,000 g Part Number Description Size Si-Propylsulfonic Acid (SCX-2) 25 g Si-Propylsulfonic Acid (SCX-2) 100 g ISOLUTE SI-Thiol 10 g ISOLUTE SI-Thiol 25 g ISOLUTE SI-Thiol 100 g ISOLUTE SI-Thiol 500 g ISOLUTE SI-Thiol 1,000 g ISOLUTE SI-Thiol 5,000 g ISOLUTE SI-Thiol 10,000 g Appendix Solvent Compatibility of Polystyrene Resins Solvent Type Swelling Solvents Non-Swelling Solvents Hydrocarbon Toluene, xylene Hexane Chlorinated DCM, dichloromethane, chlorobenzene Ether Tetrahydrofuran (THF), Ethyl ether dioxane, diglyme Ketone Cyclohexanone Acetone Polar aprotic DMF, dimethylsulfoxide ACN (DMSO), N-methylpyrolidone (NMP) Protic Ethoxyethanol MeOH, EtOH, isopropanol, water Table 5. Solvent compatibility of polystyrene resins. Lightly cross-linked polystyrene ( PS- ) resins need to be used in solvents that swell the resin beads. Mesh Size to Microns Converter Table Mesh Micron Table 6. A table which converts the mesh sizes for resin beads to their average diameter in microns. Abbreviations ACN DBAD DCE DCM DEAD DES DEAM DIC DIEA DMA DMAP DMF EtOH acetonitrile ditertbutylazodicarboxylate 1,2 dichloroethane dichloromethane diethylazodicarboxylate diethylsilane diethanolamine diisopropylcarbodiimide diisopropylethylamine dimethylacetamide dimethylaminopyridine dimethylformamide ethanol HOAc HOBt MeOH MP NMM Py PS TBD THF TS-Cl Ts-OH acetic acid N-hydroxybenzotriaole methanol macroporous N-methyl morpholine pyridine Polystyrene 1,5,7-triazabicyclo[4.4.0]dec-5-ene tetrahydrofuran toluenesulfonyl chloride toluenesulfonic acid 7
8 Solid-Supported Reagents Page 8 Your Complete Partner for Effective Chemistry Biotage is a worldwide supplier of instruments and accessories designed to facilitate the work of laboratory chemists. With our deep knowledge of the industry, academic contacts and in-house R&D teams, we can deliver the best solutions to your challenges. We take great pride in our flexibility and ability to meet our customer s individual needs. With strong foundations in both analytical and organic chemistry, we can offer the widest range of solutions available on the market. EUROPE Main Office: Toll Free: Fax: Order Tel: Order Fax: order@biotage.com Support Tel: Support Fax: eu-1-pointsupport@biotage.com NORTH & Latin AMERICA Main Office: Toll Free: Fax: Order Tel: Order Fax: ordermailbox@biotage.com Support Tel: Outside US: us-1-pointsupport@biotage.com JAPAN Tel: Fax: jp_order@biotage.com jp-1-pointsupport@biotage.com China Tel: Fax: cn_order@biotage.com cn-1-pointsupport@biotage.com To locate a distributor, please visit our website at Part Number: PPS Biotage. All rights reserved. No material may be reproduced or published without the written permission of Biotage. Information in this document is subject to change without notice and does not represent any commitment from Biotage. E&OE. Product and company names mentioned herein may be trademarks or registered trademarks and/or service marks of their respective owners, and are used only for explanation and to the owners benefit, without intent to infringe. For more information visit Biotage 2014
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