Trimethylphosphine → (S)-2-[[1-(2-aminoethyl)cyclopentanecarbonyl]amino]-3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid

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Reaction Steps

To a suspension of N-[[1-(2-azidoethyl)cyclopentyl]carbonyl]-4-[[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine on Wang resin (9.33 mmol, 13.43 g, 0.695 mmol per g) in THF (60 mL) was added a solution of 1.0 M trimethylphosphine in THF (37.3 mmol, 37.3 mL) at 0° C. The mixture was allowed to warm to room temperature and stir for 4 h at which time a Kaiser test was possitve for amine. The resin was filtered and was washed with DMF (4×20 mL), dichloromethane (4×10 mL), isopropanol (4×10 mL), DMF (2×20 mL) and dichloromethane (2×20 mL), respectively. After drying under high vacuum, 13.43 g of N-[[1-(2-aminoethyl)cyclopentyl]carbonyl]-4-[[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine on Wang resin was obtained.

Provenance & Evidence