Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrazine | HCID 9321 | — |
| Reactant | HCID 67288462 | HCID 67288462 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 178516766 | HCID 178516766 | 77% |
Reaction Steps
To a solution of methyl 2-(2-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)acetamido)acetate (compound 54, 1.1 g, 1.44 mmol) in MeOH (20 ml) was added hydrazine anhydrous (2 ml) at room temperature. Then, the reaction temperature was raised to 60° C., and maintained for overnight. After reaction complete, the solution was evaporated in vacuo, and the residue was dissolved in acetic acid (10 ml) with ammonium acetate (1 g). The reaction solution was refluxed for 1 day. The resulting solution was cooled to room temperature, and then evaporated under reduced pressure. The residue was purified with column chromatography (Hx/EtOAc=1/1) to afford to title compound (826 mg, 77% overall yield) as white solid.
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-c09b57ecb6f04c94b4bf3ac0aaa9a527 |
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| Source note | uspto-grants-2013_09 |
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