Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Isobutyl chloroformate | HCID 62365 | — |
| Reactant | tert-Butyl carbazate | HCID 70091 | — |
| 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 86701380 | HCID 86701380 | 111.4% |
Reaction Steps
To a solution of the carboxylic acid (6b, 371 mg, 1.34 mmol) of Example 9 or 16 in tetrahydrofuran (7 mL) were added triethylamine (0.227 mL) and isobutyl chloroformate (218 μl) under ice-cooling, followed by stirring at 0° C. for 15 minutes. To the reaction solution was added t-butyl carbazate (245 mg) at 0° C., followed by stirring at room temperature for 1.5 hours, and then concentrating under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1-0/1) to afford 583 mg of the title compound (yield 98%).
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-86e9e80f340940a6b837ac412d509c9e |
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| Source note | uspto-grants-2015_11 |
|---|
