Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 58505759 | HCID 58505759 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 58505684 | HCID 58505684 | 22% |
Reaction Steps
A solution of ethyl 3-{3-[(4-chlorophenyl)carbonyl]-1-(3,3-dimethylbutanoyl)-7-(quinolin-2-ylmethoxy)indolizin-2-yl}-2,2-dimethylpropanoate (39 mg, 0.06 mmol) in THF (1 mL), MeOH (1 mL), and 6M aqueous NaOH (1 mL) is heated at 70° C. for 2.5 h then cooled to 23° C. and acidified to pH=1 with 6 M aqueous HCl. The mixture is partitioned between CH2Cl2 and brine then the organics are collected and dried with MgSO4, filtered, and concentrated in vacuo. The crude is purified by flash chromatography (SiO2, CH2Cl2 to 10% MeOH in CH2Cl2) to give the title compound (8 mg, 22%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08618300B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-b85b289ba2f24a229e1e71e7bbc67f9c |
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| Source note | uspto-grants-2013_12 |
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