Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | HCID 68009052 | HCID 68009052 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 68008615 | HCID 68008615 | 99.7% |
Reaction Steps
To (2R,6S,13aS,14aR,16aS)-ethyl 6-(tert-butoxycarbonylamino)-12,12-difluoro-2-hydroxy-5,16-dioxooctadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (Example 7i, 900 mg, 1.693 mmol) was added tetrahydrofuran (5.6 ml), methanol (2.80 ml) and water (2.80 ml). Lithium hydroxide monohydrate (145.44 mg, 3.47 mmol) was added at room temperature, and the reaction mixture was stirred at 40° C. for 16 h. The reaction mixture was diluted with CH3CN and neutralized with HCl (2 N, 1.7 ml). The mixture was concentrated under reduced pressure and azeotroped with chloroform followed by ethyl acetate and dried overnight at reduced pressure to provide the title compound (850 mg, quantitative yield). This material was utilized in subsequent reactions without additional purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08937041B2 |
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| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-c4f3dde632c5490bbe6b3135b7da677b |
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| Source note | uspto-grants-2015_01 |
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