Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Chloroform | HCID 6212 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Bromomethyl acetate | HCID 68536 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 72700712 | HCID 72700712 | — |
| Catalyst | Tetrabutylammonium hydrogen sulfate | HCID 94433 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 118194560 | HCID 118194560 | 19% |
Reaction Steps
To Compound 1 (130 mg, 0.235 mmol), water (10 mL), sodium hydrogen carbonate (200 mg, 2.33 mmol), chloroform (5 mL), tetrabutylammonium hydrogen sulfate (80 mg, 0.235 mmol), and bromomethyl acetate (0.120 mL, 1.22 mmol) were added, and the resulting mixture was vigorously stirred at room temperature for 3 hours. To the reaction mixture, a saturated aqueous ammonium chloride solution was added, and the resulting mixture was extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then, the solvent was evaporated under reduced, pressure. The resulting residue was purified by silica gel column chromatography (n-hexane/ethyl acetate), whereby Compound 27 (31.9 mg, 18%) and Compound 29 (23.9 mg, 19%) were obtained, respectively.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09260459B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-c746e8ac44794297be4c611a943e769b |
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| Source note | uspto-grants-2016_02 |
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