Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Chlorobenzoyl chloride | HCID 8501 | — |
| Reactant | Stannous chloride dihydrate | HCID 61436 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 21103276 | HCID 21103276 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 21103259 | HCID 21103259 | 91.6% |
Reaction Steps
The compound of Example 56 (0.55 g, 1.2 mmol) was put into 10 mL of a MeOH solution to which SnCl2.2H2O (1.1 g, 4.8 mmol) was added, and stirred for 1 hour while maintaining the temperature at 50° C. A saturated NaHCO3 aqueous solution was introduced and the mixture was stirred for 1 hour, and then it was extracted with ethyl acetate. After distillation under reduced pressure and vacuum drying, the mixture was dissolved in 20 mL of dichloromethane and Et3N (0.41 mL, 2.9 mmol), and 4-chlorobenzoyl chloride (0.31 mL, 2.4 mmol) was added while maintaining the temperature at 0° C. After reaction for 6 hours, the reactant was washed with a saturated NaHCO3 aqueous solution and a 1N HCl aqueous solution, and dried and concentrated under reduced pressure. It was then recrystallized with hexane and ethyl acetate to obtain a white solid (0.62 g, 91%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07223751B2 |
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| Source dataset | uspto-grants-2007_05 |
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| ORD ID | ord-b185b26efe3e42a68fd14e8d745d0d63 |
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| Source note | uspto-grants-2007_05 |
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