Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Methyl 2-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)-2-(7-methylbenzo[e][1,2,4]triazin-3-yl)acetate | HCID 67287553 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67288325 | HCID 67288325 | 73% |
Reaction Steps
Sodium hydroxide (40 mg, 0.81 mmol) was added to methyl 2-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)-2-(7-methylbenzo[e][1,2,4]triazin-3-yl)acetate (compound 62, 228 mg, 0.27 mmol) in the mixture of THF, MeOH and water (9/1/1 ratio) at room temperature, and then the mixture was stirred at 70° C. for a 1 day until starting material was disappeared. After reaction complete, the solution was work-up with CH2Cl2. After evaporating the volatile solvent, silica gel column chromatography (Hx/EtOAc=⅓) gave the desired compound (115 mg, 73% yield) as light yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08541380B2 |
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| Source dataset | uspto-grants-2013_09 |
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| ORD ID | ord-178beb9bdf794efaa15a8c3bcd569f8c |
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| Source note | uspto-grants-2013_09 |
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