Ammonium Chloride → HCID 86345811, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of compound 89a (107 mg, 0.183 mmol) in 18 mL of THF at 0° C. was added LiAlH4 (0.183 mL, 0.183 mmol, 1.0M in THF). The reaction was stirred at 0° C. for 3 h. The mixture was treated with 20 mL of saturated NH4Cl solution and then extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine (10 mL), dried over Na2SO4, and filtered. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel (0-100% EtOAc/heptane) to give compound 89b as an off white solid. 1H-NMR (2:1 CDCl3/CD3OD; 400 MHz) δ: 8.34 (s, 1H), 7.76 (d, J=8.8 Hz, 1H), 7.65 (s, 1H), 7.34 (s, 1H), 6.88 (d, J=8.8 Hz, 1H), 4.78 (br. s., 6H), 3.68 (d, J=3.2 Hz, 4H), 3.60 (br. s., 4H), 3.23 (br. s., 4H), 1.51 (s, 9H). Mass spectrum (LCMS, ESI pos.): Calcd. for C25H33N7O5S, 544.2 (M+H). found 544.3.

Provenance & Evidence