Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | HCID 59505444 | HCID 59505444 | — |
| Solvent | Methanol tetrahydrofuran water | HCID 21892291 | — |
| Product | HCID 59505190 | HCID 59505190 | 98% |
Reaction Steps
Methyl 3-(2-chlorobenzamido)-1,1-dimethyl-2,3-dihydro-1H-indene-5-carboxylate (B-39) (120 mg, 0.34 mmol, 1 eq.) was dissolved in a mixture of solvents THF:MeOH:H2O (5:3:1, 5 ml) and LiOH (70 mg, 1.67 mmol, 5 eq.) was added portionwise at 0° C. The reaction mixture was stirred for 4 h and then the solvent was evaporated under reduced pressure. Water (4 ml) was added to the reaction to get a clear solution and it was then acidified with citric acid. This was followed by extraction with EtOAc (2×50 ml). The organic part was washed with brine (20 ml), dried over Na2SO4, filtered and evaporated under reduced pressure to yield the crude product which was purified by column chromatography (silica gel, 5% MeOH/MC) to yield the desired product as a white solid. Yield: 98% (115 mg, 0.34 mmol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08455475B2 |
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| Source dataset | uspto-grants-2013_06 |
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| ORD ID | ord-5bda4e6c94d54b0a90308722e12f2991 |
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| Source note | uspto-grants-2013_06 |
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