Sodium Iodide → HCID 69494587, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 250 mg of efavirenz in 10 mL of anhydrous DMF was added 600 mg of anhydrous K2CO3, 120 mg NaI, 490 mg of 2-(BOC-amino)ethyl bromide and 5 mg of 18-crown-6. The reaction mixture was heated at 125° C. for 2 hours. The reaction mixture was cooled to room temperature, and 1 g of 2-(BOC-amino)ethyl bromide and 20 mg of tetrabutylammonium iodide were added and allowed to stir at room temperature 18 hours. The reaction mixture was analyzed by reverse-phase high performance liquid chromatography (RP-HPLC, C-18 Vydac 218TP54 (4.6 mm×250 mm) using a gradient run with water-acetonitrile mixtures containing 0.1% trifluoroacetic acid (0-100% AcCN-0.1% TFA in 20 minutes). This indicated the formation of product with a substantial amount of efavirenz in the reaction mixture. An additional 1 g of 2-(BOC-amino)ethyl bromide was added, and the reaction mixture was heated at 60° C. for 18 hours. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated, and the residue was purified by preparative RP-HPLC using a gradient run (CH3CN/water containing 0.1% trifluoroacetic acid). The column used was a Rainin C-18 (ODS) 60 Å (21.4×250 mm). The desired fractions were combined, concentrated in the rotary evaporator, and then lyophilized to give 25 mg of the desired product 7 as a white solid (M+Na, 481).

Provenance & Evidence