Sodium Thiosulfate → HCID 18752818, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-[2-(3-(2-propylamino)-3-oxo-2,2-difluoro-1-hydroxypropyl)phenyl]-2-methoxyphenylcarboxamide of Step 4 (200 mg, 0.51 mmol), CH2Cl2 (5 mL) and tert-butanol (5 mL), was added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxyl-3(1H)-one (1.5 g, 3.54 mmol) under argon at 23° C. After 18 h, sat. NaHCO3 (10 mL) was added followed by solid Na2S2O3 (1.0 g, 6.3 mmol). After 2 h of vigorous stirring at 23° C., the organic layer was separated, washed with sat. NaHCO3 (2×10 mL), sat. Na2S2O3 (2×10 mL), and brine (1×10 mL) and dried (MgSO4). Upon concentration in vacuo and trituration with ethyl ether, the title compound was afforded (100 mg) as a yellow solid : mp 131.5-132° C. 1H NMR (CDCl3) δ1.27 (d), 4.13 (s,), 4.13-4.20 (m), 6.32 (br d), 7.04 (m), 7.10 (m), 7.19 (m), 7.51 (m) 7.67 (m), 8.11 (m), 8.22 (m), 8.90 (m), 12.01 (br s). MS (EI) 390 (M+), 254, 135. Anal. Calc'd. for C20H20F2N2O4 plus 0.25 mol H2O: C, 60.83; H, 5.23; N, 7.09. Found: C, 60.75; H, 5.00; N, 6.95.

Provenance & Evidence