Triphenylphosphine → HCID 178512850, compound

Participants

Reaction Steps

Rink resin (500 mg; loading 0.3 mmol/g) functionalized with Arg(Boc)2 was coupled with 176 mg of 3,5-dihydroxy-4-bromobenzoic acid in the presence of DIC (110 mg) and HOBt (78 mg) in DMF. The resin was then washed and treated with a 30% solution of benzyltrimethylammonium hydroxide in DMF for 1 h. The resin was washed with DMF, 10% acetic acid in DMF, DMF, and DCM and dried in vacuo for 3 h. The dried resin was washed with anhydrous THF and mixed with 0.2 mmol of triphenylphosphane and 0.2 mmol of 2-(2,4-dichlorophenyl)ethanol in 2 ml of dry THF. The suspension of the resin was cooled in a refrigerator for 16 min and 50 μl (0.2 mmol) of DIAD in 0.5 ml of dry THF were added. Coupling was continued overnight at room temperature. The resin was washed with dry THF and the coupling was repeated for additional 8 h. The resin was washed and dried, and the final product was cleaved off and processed as described in Example 1.

Provenance & Evidence