Hydrochloric Acid → HCID 135862883, compound

Participants

Reaction Steps

tert-Butyl 4-formyl-2,2-dimethylthiazolidine-3-carboxylate (750 mg, 3.06 mmol) was suspended in isopropanol (20 mL) and stirred under nitrogen at room temperature. HCl (2.3 mL, 4.0 M dioxane solution) was added dropwise and the reaction was stirred for 16 h. To the reaction mixture a solution of TCEP (1.49 g, 5.2 mmol) in 5 mL water was added. The pH of the reaction was adjusted to ca. 8 with a solution of saturated sodium carbonate. A solution of 6-hydroxy-benzo[d]thiazole-2-carbonitrile (590 mg, 3.35 mmol) in THF (5 mL) was added dropwise and the reaction was stirred for 20 hours. The reaction was stopped when HPLC analysis showed no more progress. The solvent was evaporated in vacuo and the resulting yellow residue was taken up in acetonitrile:water (1:1) and purified by reverse phase chromatography using a 50 mM TEAA/ACN gradient from 90/10 to 100% ACN over 30 minutes. Evaporation of the solvent afforded 300 mgs of the desired product. 1H-NMR (300 MHz, CD2C12) □: 7.94 (d, 1H, J=9 Hz), 7.32 (d, 1H, J=2.4 Hz), 7.05 (dd, 1H, J=8.7 Hz, 2.4 Hz), 4.95 (d, 1H, J=4.5 Hz), 4.79 (1H, m), 3.90 (2H, m), 3.48 (2H, m), 1.2 (12H, m); mass spectrum, calculated for C17H23N2O3S2 (MH+) 367.1. Found 367.2.

Provenance & Evidence