HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → (5S)-9-Bromo-5-[p-tert-butoxycarbonylaminomethyl-o-(1-carboxy-1-hydroxymethyl) phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | (5S)-9-Bromo-5-[p-tert-butoxycarbonylaminomethyl-o-(1-methoxycarbonyl-1acetoxymethyl) phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione | HCID 131720488 | — |
| Solvent | Sodium Hydroxide | HCID 14798 | — |
| Product | (5S)-9-Bromo-5-[p-tert-butoxycarbonylaminomethyl-o-(1-carboxy-1-hydroxymethyl) phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione | HCID 131720489 | 97.2% |
Reaction Steps
A solution of (5S)-9-bromo-5-[p-tert-butoxycarbonylaminomethyl-o-(1-methoxycarbonyl-1-acetoxymethyl)phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (310 mg, 0.46 mmol) in a mixture of 1N aqueous sodium hydroxide (6 mL), THF (5 mL), and methanol (5 mL) was stirred for 6 h at room temperature. The mixture was concentrated to ca. 6 mL and acidified with 5% aqueous potassium hydrogen sulfate. The precipitates formed were collected and dried to give 276 mg of the title compound (97%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05719152 |
| Source dataset | uspto-grants-1998_02 |
| ORD ID | ord-7b0e9498b4804b1e960b0bf43e3a1fa0 |
| Source note | uspto-grants-1998_02 |