Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | HCID 131732775 | HCID 131732775 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 117776457 | HCID 117776457 | 61.8% |
Reaction Steps
To a solution of compound (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-(2-(methoxyimino)-2-phenylethoxy)benzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate (170 mg, 0.23 mmol) in MeOH:THF:H2O (0.7 mL, 0.5 mL, 0.17 mL), LiOH.H2O (14.7 mg, 0.35 mmol) was added at 0° C. The reaction mixture was stirred for 1 h at r.t. After completion of the reaction as confirmed by TLC, solvent was evaporated in vacuo. The residue obtained was diluted with ethylacetate (100 mL), washed with water (10 mL) and brine (10 mL). The organic layer was dried over Na2SO4 and the volatiles were evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, MeOH:DCM) to afford the title compound (80 mg, 0.14 mmol, 61.8%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09018249B2 |
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| Source dataset | uspto-grants-2015_04 |
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| ORD ID | ord-1c7b5eaf9e2c4fe8b144e699d5505c2e |
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| Source note | uspto-grants-2015_04 |
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