Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | HCID 59314084 | HCID 59314084 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 59314229 | HCID 59314229 | 80% |
Reaction Steps
A mixture of 2-[(6-tert-butyl-1,1-dimethyl-indane-4-carbonyl)-amino]-indan-2-carboxylic acid methyl ester (600 mg, 1.4 mmol) and KOH (1.8 g, 30.8 mmol) is dissolved in EtOH (25 mL) and water (2 mL) under water bath. The water bath is removed when KOH is completely dissolved and the resulting reaction solution is stirred at RT for 8 h. After concentration in vacuo, the residue is neutralized with 1N HCl and extracted with EtOAc (3×150 mL), the organic washes are combined and concentrated in vacuo. The residue is purified by preparative HPLC (C18 column 10 micron, gradient elution: 20-100% ACN 0.1% TFA in H2O 0.1% TFA). Product crystallizes out of the collected fractions on standing. Filtration and drying gave pure product as white solid (454 mg, 78%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08569535B2 |
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| Source dataset | uspto-grants-2013_10 |
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| ORD ID | ord-3a9af32eb5b74c05b84b4446d4d01cf6 |
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| Source note | uspto-grants-2013_10 |
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