Isopropanol → HCID 145857632, compound

Participants

Reaction Conditions

Reaction Steps

The {[4-(5′-hydroxymethyl-2′-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester ((Example 7: step b) 30 mg, 0.056 mmol) was dissolved in a mixture of DMSO (1 mL) and DCM (1 mL) and cooled to 0° C. Triethylamine (12 μL, 0.084 mmol) and sulfur trioxide-pyridine complex (11 mg, 0.068 mmol) were added and the solution was stirred for 1 h at 0° C. Partial conversion was evident by TLC. Additional triethylamine (20 μL, 0.14 μL) and sulfur trioxide-pyridine complex (18 mg, 0.11 mmol) were added and the solution was stirred for 3 h at rt. Isopropanol (250 μL) was added, the reaction was stirred for 15 min, and EtOAc (40 mL) was added. The EtOAc solution was extracted with citric acid (2×10 mL), NaHCO3 (2×10 mL), water (5×10 mL), and brine (20 mL), and was dried over sodium sulfate. Removal of the solvent in vacuo yielded the title compound (26 mg, 87%) which was used without further purification. 1H-NMR (CD3OD): δ 10.00 (s, 1H), 7.99 (m, 3H), 7.81 (dd, 1H, J=1.6 7.7 Hz), 7.72 (d, 1H, J=7.7 Hz), 7.59 (m, 2H), 7.46 (d, 1H, J=7.7 Hz), 2.58 (s, 3H), 2.30 (s, 3H), 1.51 (s, 9H).

Provenance & Evidence