HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → Methyl(2S,3S,5S)-5-(3-fluorophenoxy)-3-[(hydroxyamino)carbonyl]-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Hydroxylamine | HCID 787 | — |
| Reactant | Sodium Methoxide | HCID 10942334 | — |
| Reactant | Dimethyl (2s,3s,5s)-5-(3-fluorophenoxy)-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate | HCID 67304243 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | Methyl(2S,3S,5S)-5-(3-fluorophenoxy)-3-[(hydroxyamino)carbonyl]-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1-carboxylate | HCID 86598247 | 54.5% |
Reaction Steps
To a solution of dimethyl(2S,3S,5S)-5-(3-fluorophenoxy)-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate (27 mg, 0.000054 mol) in methanol (0.2189 mL, 0.005405 mol) was added 1.640 M of N-hydroxyamine in Methanol (0.659 mL) made from the corresponding HCl salt and sodium methoxide. After stirred at rt for 1 h, the mixture was acidified with 1N HCl. The resultant mixture was applied directly on RP-HPLC to afford the product as a TFA salt (18 mg 54.5%). MS (ESI): (M+H)+=501.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09440958B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-f34f048bcf3240a7823224f5685bfeb6 |
| Source note | uspto-grants-2016_09 |