Triphenylphosphine → HCID 59104364, compound

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.[C:9]([O:13][C:14](=[O:25])[NH:15][CH:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:17]O)([CH3:12])([CH3:11])[CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:9]([O:13][C:14](=[O:25])[NH:15][C@@H:16]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:17][O:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)([CH3:10])([CH3:11])[CH3:12]

Participants

Procedure

A solution of 5-bromo-pyridin-3-ol (0.3 g, 1.7 mmol), (2-hydroxy-1-phenyl-ethyl)-carbamic acid tert-butyl ester (0.41 g 1.7 mmol), and triphenylphosphine (0.52 g, 2 mmol) in THF (15 mL) was stirred at 0° C. for 30 min. To the mixture was added a solution of di-t-butyl azidodicarboxylate (0.46 g, 2 mmol) in 5 ml of THF. The mixture was allowed to warm to room temperature then stirred at room temperature for 20 h. The THF was evaporated off and the residue was taken into ethyl acetate (75 ml), washed with saturated sodium bicarbonate (50 ml) water (50 ml) and brine (50 ml). The ethyl acetate was evaporated off and the residue was purified by flash column chromatography on silica gel, eluting with a solvent gradient of 1:4 to 1:2 ethyl acetate/hexane. Recovered 0.82 g of a mixture of product and di-tert-butyl azidodicarboxylate. MS (ESI) m/z 395 (M+H)+.