Triphenylphosphine → HCID 21310745, compound

Participants

Reaction Steps

To a suspension of (5-pyridin-2-yl-thiophene-2-sulfonyl)-amino]-N-hydroxy-3-methyl-benzamide on Wang resin, the product of Example 407 (100 mg, 0.84 mmol/g), in a solution of 3,4 dimethylbenzyl alcohol (0.485 mmol) in THF (1 mL) was added a solution of triphenylphosphine (0.485 mmol) and diethyl azodicarboxylate (0.485 mmol) in THF (1.24 mL). The resultant mixture was shaken for 4 h at room temperature. The resin was filtered, washed with THF (4×3 mL) and dichloromethane (4×3 mL), and dried under vacuum. The resin was suspended in trifluoroacetic acid/ dichloromethane (1:1, 2 mL) and allowed to sit for 1 h. The resin was filtered and washed with DCM (2×1.5 mL). The combined filtrates were evaporated to dryness, and the crude product was purified on a solid phase extraction cartridge (reverse phase) to give 18.1 mg of product Mass Spec: expected 507.1286, found 507.9.

Provenance & Evidence