Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 89445477 | HCID 89445477 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 117761986 | HCID 117761986 | 96% |
Reaction Steps
To a solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-(2-((tert-butyl dimethyl silyl)oxy)ethoxy)benzyl)-4-cyanophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (180.0 mg, 0.25 mmol), was added acetic acid (1.5 mL) and water (0.5 mL) and the reaction mixture was stirred overnight at r.t. After the completion of the reaction as confirmed by TLC, the reaction mixture was diluted with ethyl acetate (50 mL) followed by neutralization with sodium bicarbonate solution till effervescence ceased. The organic layer was separated, washed with water (2×20 mL), dried over Na2SO4 and concentrated in vacuo to afford crude product which was purified by column chromatography (silica gel, 3:2 EtOAc:Pet Ether) to afford title compound (140.0 mg, 95%) as a solid.
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-94d36e4493ed4020b92d4765b73f3adc |
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| Source note | uspto-grants-2015_04 |
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