Thiazolidine → HCID 57945087, compound

Participants

Reaction Steps

A solution of 35 mg (0.046 mmol) of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-[4-(3-iodopropoxy)benzyl]propylcarbamate, 11 μL (0.14 mmol) of thiazolidine, and 32 μL (0.18 mmol) of N,N-diisopropylethylamine in 0.5 mL of anhydrous DMF was heated to 80° C. with stirring. After 1.5 hours TLC indicated the reaction to be complete. The solution was cooled to RT and concentrated in vacuo. The residue was subjected to flash chromatography (SiO2, 95:5 CH2Cl2/MeOH) to afford 22 mg (67%) of the desired compound as a white foam. 1H NMR (CDCl3): 7.29 (d, 1H), 7.13 (s, 1H), 7.08 (d, 2H), 7.85 (d, 1H), 6.77 (d, 2H), 6.04 (s, 2H), 5.60 (d, 1H), 5.00 (q, 1H), 4.88 (d, 1H), 4.01 (s, 2H), 4.00-3.88 (m, 3H), 3.80 (m, 3H), 3.67 (m, 2H), 3.55 (br s, 1H), 3.19-3.01 (m, 4H), 3.00-2.65 (m, 7H), 2.52 (t, 2H), 1.93 (m, 2H), 1.79 (m, 1H), 1.70-1.42 (m, 2H), 0.89 (d, 3H), 0.83 (d, 3H). MS(ESI): 722(M+H).

Provenance & Evidence