Piperidine → HCID 15431840, compound

Participants

Reaction Steps

Ala-Phe-Leu-Pro-Ala-WANG resin (SEQ ID NO:5) was prepared starting from Fmoc-Ala-WANG resin (0.44 mmol/gram) using standard Fmoc-SPPS protocols, with HBTU coupling and piperidine deprotection as described in Example 1. To 500 mg of this resin, a solution of 300 mg o-nitrobenzenesulfonylchloride in DMF (4 mL) containing DIEA (200 μL) was added. After 30 minutes, the resin was drained and washed with DMF (3×). The resin was mixed with a solution of S-(p-methylbenzyl)-2-mercaptoethanol (270 mg, 1.5 mmol) in DCM (5 mL). Triphenylphosphine (393 mg, 1.5 mmol) and diethylazodicarboxylate (DEAD, 261 mg, 1.5 mmol) were premixed in DCM (5 mL). After 1 minute, the solution was added to the resin and the reaction left for 30 minutes. The resin was washed with DCM (3×) and DMF (3×). The resin was further treated with a solution of NaSPhe (200 mg, 1.5 mmol) in DMF (4 mL) for 30 minutes. The resin was washed with DMF (3×) and MeOH/DCM (3×) and air dried.

Provenance & Evidence