Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Methyl chloroformate | HCID 6586 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 71224956 | HCID 71224956 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | HCID 71224690 | HCID 71224690 | 96% |
Reaction Steps
2 mL of a chloroform solution containing 0.24 g (1 mmol) of 2-t-butoxycarbonyl amino-6-methylpyridine and 0.26 g (2 mmol) of diisopropylethylamine was prepared, and was cooled in ice water. The above mixed solution was added dropwise at 0° C. to 0.3 mL of a chloroform solution containing 0.11 g (1.2 mmol) of methyl chloroformate. After stirring further for 20 minutes, the temperature was raised to room temperature. After stirring further for 5 hours at room temperature, 5 mL of water and 1 mL of 3N hydrochloric acid were added thereto, followed by liquid separation. The organic layer obtained by liquid separation was dried with magnesium sulfate, followed by filtration, and the resulting solution was concentrated under reduced pressure to obtain 0.27 g of 2-t-butoxycarbonyl-methoxycarbonyl amino-6-methyl pyridine-N-oxide (yield: 96%) as a pale yellow oily liquid which was the target product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08962850B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-9b3a0b9d5ebd45fb95787d0753fd91d5 |
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| Source note | uspto-grants-2015_02 |
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