Monoacylation of unprotected symmetrical diamines with resin-bound benzoic acids |
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Authors: | Yonghui Wang Jian Jin Todd L Graybill Michelle A Wang Qian Jin |
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Institution: | a High Throughput Chemistry, GlaxoSmithKline, 1250 S. Collegeville Rd, Collegeville, PA 19426, USA b Computational, Analytical and Structural Sciences, GlaxoSmithKline, 1250 S. Collegeville Rd, Collegeville, PA 19426, USA |
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Abstract: | A protocol for monoacylation of unprotected symmetrical diamines with a resin-bound benzoic acid is described. The nature of the resin (gel-based polystyrene vs highly crosslinked macroporous polystyrene) was found to play a minor role in acylation selectivity. Rather, the concentration of the diamine dictates the ratio of mono- and diacylated products. Thus, by employing a high concentration of symmetrical diamine (e.g., 1 M, 20 equiv), monoacylation can be selectively achieved for a variety of unprotected symmetrical alkyl and aryl diamines. |
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Keywords: | Monoacylation Diacylation Crosslinking Symmetrical diamines Resin comparison Concentration effect Solid phase reaction |
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