Pyridine → HCID 70196286, compound

Participants

Reaction Conditions

Reaction Steps

1(3-O-Benzoyl-6-phthalimido-2,4,6-trideoxy-β-D-threo-hexopyranosyl)-1H-indole (0.30 g, 0.62 mmol) was dissolved in dichloromethane (3 ml) and cooled to 0° C. Oxalyichloride (65 μl, 0.74 mmol) was added and the reaction mixture kept at 0° C. for 15 ml and then stirred at room temperature for another 45 minutes. N-hydroxysuccinimid (0.08 g 0.70 mmol) was added followed by careful addition of pyridine (0.10 ml, 1.23 mmol). The reaction mixture was stirred at room temperature for 16 hours and then washed twice with water. The organic layer was evaporated and the crude mixed with tetrahydrofuran (10 ml) and 1,2-diphenylenediamine (0.09 g, 0.80 mmol) and stirred at room temperature for 16 hours. The resulting percipitate was collected by centrifugation, washed twice with ether and dried to give 0.12 g (32%) of the subtitle product.

Provenance & Evidence