Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzoyl chloride, 3-nitro- | HCID 8495 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 3-(Aminomethyl)-1-N-Boc-aniline | HCID 2756481 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 57961674 | HCID 57961674 | 105% |
Reaction Steps
A solution of tert-butyl [3-(aminomethyl)phenyl]carbamate (2.0 g, 9 mmol) and triethylamine (1.3 mL, 9.5 mmol) in tetrahydrofuran (26 mL) at 0° C. was treated with a solution of 3-nitrobenzoyl chloride (1.8 g, 9.5 mmol) in tetrahydrofuran (7.3 mL) and stirred at 20° C. for 1 h. The reaction mixture was treated with saturated sodium bicarbonate and the aqueous layer was separated and extracted with ethyl acetate (3×15 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and evaporated to give the desired product (3.5 g, 105%) as a crude off-white solid that was used without further purification. LCMS for C15H14N3O5 ([M-(t-Bu)+H]+H)+: m/z=316.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08871753B2 |
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| Source dataset | uspto-grants-2014_10 |
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| ORD ID | ord-cba1d40832694c79960032eda8aa1b93 |
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| Source note | uspto-grants-2014_10 |
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