Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Acetohydrazide | HCID 14039 | — |
| Reactant | Isobutyl chloroformate | HCID 62365 | — |
| Reactant | (2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid | HCID 57389355 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86694021 | HCID 86694021 | 92% |
Reaction Steps
To a solution of the carboxylic acid (6b, 2.37 g, 8.57 mmol) of Example 9 or 16 in tetrahydrofuran (50 mL) were added triethylamine (1.39 mL) and isobutyl chloroformate (1.32 mL) under ice-cooling, followed by agitating at 0° C. for 20 minutes. To the reaction solution was added acetohydrazide (807 mg) at 0° C., stirred at room temperature for 40 minutes and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1) to afford 2.61 g of the title compound (yield 92%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09181250B2 |
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| Source dataset | uspto-grants-2015_11 |
|---|
| ORD ID | ord-76f743aa357d4c1e8ac2c5cb5022f26b |
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| Source note | uspto-grants-2015_11 |
|---|
