Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzyl chloroformate | HCID 10387 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 59323140 | HCID 59323140 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59323111 | HCID 59323111 | 93% |
Reaction Steps
31.5 mg of N-[3,5-bis(tert-butyloxycarbonyl)aminobenzyl]-2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine was taken into a 20-mL eggplant flask and dissolved in 1.5 mL of dichloromethane, and 0.01 mL of triethylamine and 0.01 mL of Cbz-chloride were sequentially added thereto under ice-cooling, followed by stirring for 1 hour at room temperature. After completion of the reaction, to the reaction liquid were added a saturated aqueous sodium bicarbonate solution and chloroform under ice-cooling. The organic layer was separated, the aqueous layer was further extracted by addition of chloroform, and the organic layer was combined and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the solvent was removed by evaporation to obtain 120.0 mg of a crude composition. The crude composition was purified by PLC to obtain 35.8 mg (yield 93%) of a title compound as a pale yellow oily substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08273766B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-5b5cc1402b08462d9f97b063673b23a4 |
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| Source note | uspto-grants-2012_09 |
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