Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanolamine | HCID 700 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 4-(((tert-Butoxycarbonyl)amino)methyl)benzoic acid | HCID 853605 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67634939 | HCID 67634939 | 95.2% |
Reaction Steps
2.06 g (8.21 mmol) of 4-[(tert-butoxycarbonylamino)methyl]benzoic acid suspended in 40 mL of methylene chloride was mixed with 1.63 g (10.1 mmol) of 1,1′-carbonyldiimidazole at room temperature and stirred at room temperature for 1.5 hours. The reaction solution was further stirred with 1.8 mL (30 mmol) of 2-aminoethanol overnight, and after addition of 40 mL of saturated aqueous sodium hydrogen carbonate, 20 mL of water and 200 mL of methylene chloride, was allowed to separate. The organic layer was washed with 80 mL of 1 M hydrochloric acid, with 40 mL of saturated aqueous sodium hydrogen carbonate and with 20 mL of saturated aqueous sodium chloride twice, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain the desired product (2.30 g, yield 95%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08889732B2 |
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| Source dataset | uspto-grants-2014_11 |
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| ORD ID | ord-81a8792cc6ff4c44bac37c0473162863 |
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| Source note | uspto-grants-2014_11 |
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