HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → (2R,3S)-3-amino-8-[6-(methyloxy)-1,5-naphthyridin-4-yl]-8-azaspiro[4.5]decan-2-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | 1,1-dimethylethyl {(2S,3R)-3-hydroxy-8-[6-(methyloxy)-1,5-naphthyridin-4-yl]-8-azaspiro[4.5]dec-2-yl}carbamate | HCID 57842932 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | Carbonate Ion | HCID 19660 | — |
| Product | (2R,3S)-3-amino-8-[6-(methyloxy)-1,5-naphthyridin-4-yl]-8-azaspiro[4.5]decan-2-ol | HCID 57842930 | 47.4% |
Reaction Steps
To a solution of 1,1-dimethylethyl {(2S,3R)-3-hydroxy-8-[6-(methyloxy)-1,5-naphthyridin-4-yl]-8-azaspiro[4.5]dec-2-yl}carbamate (220 mg, 0.514 mmol) in MeOH (5 mL) at 25° C. was added a solution of 4M HCl in dioxane (900 μL, 3.60 mmol). After 12 h, the solution was concentrated and the residue neutralized using excess MP carbonate resin yielding the title compound (80 mg, 47%) as an orange oil: LCMS (ES) m/e 329 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07592334B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-ad5ccc8dfe8a4d11ae54e17826115da5 |
| Source note | uspto-grants-2009_09 |