5-[4-(9-Fluorenylmethyloxycarbonyl)aminomethyl-3,5-dimethoxyphenoxy]pentanoic Acid (PAL Linker)

Abstract

[115109-65-4] C29H31NO7 (MW 505.57) InChI = 1S/C29H31NO7/c1-34-26-15-19(36-14-8-7-13-28(31)32)16-27(35-2)24(26)17-30-29(33)37-18-25-22-11-5-3-9-20(22)21-10-4-6-12-23(21)25/h3-6,9-12,15-16,25H,7-8,13-14,17-18H2,1-2H3,(H,30,33)(H,31,32) InChIKey = ATYUCXIJDKHOPX-UHFFFAOYSA-N (acid-labile linker/handle used for solid-phase synthesis of peptide amides, and more general applications to solid-phase organic synthesis) Alternate Names: peptide amide linker, Fmoc-PAL. Physical Data: mp 178–180 °C (para), 116–118 °C (ortho). Analytically calculated for C29H31NO7 (MW 505.57): C, 68.90; H, 6.18; N, 2.77. Found: C, 68.92; H, 6.16; N, 2.80. Solubility: soluble in most polar organic solvents. Form Supplied in: the title compound is a crystalline solid. It is available in its pure para, pure ortho, or ortho/para mixture as a solid, off-resin. It can also be obtained attached to a suitable solid support. See main text for further details. Analysis of Reagent Purity: NMR, elemental analysis, TLC, or other chromatographic criteria. Preparative Methods: can be prepared in five steps in solution, starting with Vilsmeier formylation of 3,5-dimethoxyphenol. Purification: para—recrystallization from minimal hot MeOH–CHCl3 (2:1), then chilling to −20 °C; ortho—recrystallization from minimal hot MeOH. Handling, Storage, and Precautions: no special precautions are necessary. Details depend on whether the reagents are solid organic compounds or are attached to a solid support. If possible, they should be refrigerated to increase the shelf-life. Disposal: these compounds are not particularly hazardous, and standard methods for solid organic waste disposal should be adequate.