Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Chloro-1-methylpyridinium iodide | HCID 167069 | — |
| Reactant | tert-butyl N-[(4-aminophenyl)methyl]carbamate | HCID 2756041 | — |
| Reactant | (2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid | HCID 57389355 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86659591 | HCID 86659591 | — |
Reaction Steps
To a solution of (2S,5R)-6-(phenylmethoxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid (29.9 mg, 0.108 mmol) in dry dichloromethane (3 mL) was added triethylamine (0.038 mL, 0.271 mmol), 2-chloro-1-methylpyridinium iodide (41.0 mg, 0.160 mmol), and 4-(N—BOC-aminomethyl)aniline (30.6 mg, 0.138 mmol) sequentially at room temperature under nitrogen. The reaction was then heated to 60° C. for 2 hours. LC/MS showed no starting material remaining. The reaction mixture was concentrated and purified by HPLC on a Waters Sunfire column to afford the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08487093B2 |
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| Source dataset | uspto-grants-2013_07 |
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| ORD ID | ord-6b4b8ac294ac4a0bbd7544947c2f6086 |
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| Source note | uspto-grants-2013_07 |
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