Triphenylphosphine → CID 71511789

Participants

Reaction Conditions

Reaction Steps

In a 5 mL seal vial equipped with a stir bar was added (3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol (30.00 mg; 0.12 mmol; 1.00 eq.) and 1-chloropyrrolidine-2,5-dione (24.20 mg; 0.18 mmol; 1.50 eq.) in N,N-dimethylformamide (1.00 ml) followed by triphenylphosphine (63.38 mg; 0.24 mmol; 2.00 eq.). After the clear solution was stirred at 50° C. for 2 h, color became wine red. The reaction was stirred for overnight before it is concentrated and dissolved in 2 mL MeOH. Yamazen HPLC Channel1 (acidic condition, 220 nm, 55 g Interchim column, product efflux at H2O/ACN=75/25) was used to isolate 5.4 mg (12%) of the title compound as a white solid once lyophilized.

Provenance & Evidence