HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 3-Oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 5-((1R,2S)-1-tert-Butoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-3-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopent-1-enecarboxylic acid methyl ester | HCID 59204187 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 3-Oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid | HCID 46244965 | 89.3% |
Reaction Steps
Sodium hydroxide (1M, 74 mL, 0.074 mol) was added to a stirred solution of 30 (3.73 g, 0.018 mol) in methanol (105 mL) at room temperature. After 4 h, the reaction mixture was neutralized with 3M HCl, evaporated and co-evaporated with toluene several times. Pyridine (75 mL) and Ac2O (53 mL) were added and the reaction mixture was allowed to shake overnight at room temperature. The mixture was then co-evaporated with toluene and purified by flash column chromatography (ethyl acetate+1% acetic acid) to give the title compound (2.51 g, 88%) as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07700552B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-857a6a3b613749dab517a62fd97aa7e8 |
| Source note | uspto-grants-2010_04 |