Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | HCID 59180413 | HCID 59180413 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 25183376 | HCID 25183376 | 76.7% |
Reaction Steps
To a solution of 48 (256.0 mg; 0.69 mmol) in tetrahydrofuran (15 mL) and methanol (3 mL) was added aqueous lithium hydroxide (3.5 mL; 2M). The reaction mixture was heated at 75-80° C. for 6 hours, allowed to cool to room temperature and then concentrated under reduced pressure. The resulting residue was dissolved in chloroform (15 mL) and washed with aqueous hydrochloric acid (2×10 mL; 2N). The organic phase was dried over magnesium sulfate, filtered and the solvent evaporated under reduced pressure. The crude beige residue was purified by automated silica gel column chromatography (Biotage®) eluting with ethyl acetate/hexanes (0 to 10% v/v over 350 mL gradient elution) to give the title product as a white solid (187 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08178699B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-5b178449de264da88a0ef024ebbc3bf3 |
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| Source note | uspto-grants-2012_05 |
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