Table 2.
Effect of concentration of NaOH on Impurity E (1) content in the oxidation of pantoprazole sulfide (4) to pantoprazole sulfoxide (5).a
Entry | NaOH (mmol) | HPLC conversion (%) |
|||||
---|---|---|---|---|---|---|---|
Sulfoxide (5) | Imp A (7) | Sulfide/ Imp B (4) | Imp C (3) | Imp D + F (8,9) | Imp E (1) | ||
1 | 5 | 93.88 | 0.15 | 0.08 | nd | nd | 0.31 |
2 | 10 | 95.45 | nd | 0.13 | nd | nd | 0.57 |
3 | 15 | 96.12 | 0.05 | 0.20 | nd | nd | 0.64 |
4 | 20 | 96.50 | 0.03 | 0.03 | nd | 0.06 | 0.84 |
5 | 25 | 97.27 | 0.24 | 0.13 | nd | 0.05 | 0.94 |
6 | 30 | 95.01 | 0.05 | 0.18 | nd | nd | 0.89 |
nd : not detected.
Reaction conditions: 5-(difluoromethoxy)-1H-benzimidazole-2-thiol (3), 10 mmol; NaOCl, 10.5 mmol, assay 9.0%; water, 10 mL at 0–5 °C for 3 h.